Money, investments, and other financial stuff

[Blueprint]

Wife and I were minority owners (25%) of a beach house in Maine for 3 years. Despite paying local caretakers, the house basically paid itself. The partners, another couple, were not as involved as we expected them to be and while we were making our move to buy them out, the other guy had a 6th kid, but with his wife's business partner. So the house was sold off, and we made a nice profit for our efforts.

What we learned - we have the knack to manage vacation rentals (only 5 star reviews for those 3 years, returning customers), if you plan well the places will pay for themselves or even have operational profit while you build equity, but never go into business with friends if you get attached to / always dreamed of said business. Be ready to cut the ties at any time.

[Firm]

That's good advice. One important factor for me is that Mrs.Firm is currently a stay-at-home mom, and in about 1-2 years our youngest will be in school full time, which means her schedule will be a lot more flexible. I wouldn't want to take her focus off of the family, but if she had something, like a rental property(s), or similar, to manage a few hours a week, it would probably be a good thing for her.

[Blueprint]

That's good advice. One important factor for me is that Mrs.Firm is currently a stay-at-home mom, and in about 1-2 years our youngest will be in school full time, which means her schedule will be a lot more flexible. I wouldn't want to take her focus off of the family, but if she had something, like a rental property(s), or similar, to manage a few hours a week, it would probably be a good thing for her.

Similar situation here. My wife was seeing herself transitioning from her demanding healthcare work to managing our properties. Had we bought out our partners at the time, we would probably have two other units or more at this time. Back when we started, our beach house was renting at $4k USD/week. Recently - should not have looked - current owners have it at $9kUSD/week as the market went waaayyy up. But that ship has sailed, no way with could do that at today's prices, and especially not in the US - even just for the exchange rate.

[RRocket]

Who can afford $4k a week..let alone $9k a week.

[Blueprint]

Who can afford $4k a week..let alone $9k a week.

It's a big house, so in our days it rented to groups ie two families with kids, or even 4 couples. It was sold out every summer, still is. Our last year we were rented out more than 50% of the year, with variable rates per season of course. The house had a reverse plan, with living spaces on the 2nd floor. Built on a rock, from the top deck your view was over the roofs of the oceanfronts accross the street. Salty air, inexpensive wine and lobster bought at the dock ... miss that.

[Firm]

Yep, if we went that route it would be in the Pensacola / Destin area and it's similar, right now you're looking at $4-6K/week to rent something similar, and that's typically what people do, couple families, or a larger family gathering. Places are booked solid April-November.

We go a couple times a year, and have a loyalty deal with one of the resorts down there that gets us a nice ocean view balcony room for about $2500/week....But it's just a room, not a house or even a condo. Which is part of my motivation here, if I am already spending ~$5K/year on rent down there, that would cover a good chunk of my operating cost if used some cash to buy a modest beach house that we could rent when not using it.

Course, there's risk....it's dependent on the vacation market, there's hurricanes to worry about, travel back and fourth when stuff goes wrong, etc. Plus, acquisition cost is relatively high. Locally here in the Memphis area you can find newer starter-home type detached properties for ~$200K, and they rent for $2.5-3K/month....While boring, the return on something like that, is pretty good, especially if you grab 3-4 of them. 

[Gurgie]

Who can afford $4k a week..let alone $9k a week.

We spend more than that for a weekend rental when we do our guys golf trips. Last 2 years our spring golf trip was just over $5k for 2 nights in an AirBNB, but when you divide that by 16 guys, it's cheaper than a hotel room for 2 nights. We usually end up in some pretty good places that sleep 16 comfortably where we're not stuck sharing beds, plus the last two we had waterfront properties, with indoor pools, hot tubs, sauna's.

We stayed at this place 2yrs ago at the beginning of June https://www.airbnb.ca/rooms/13564326?adults=16&location=Peterborough%2C%20ON&search_mode=regular_search&check_in=2026-02-06&check_out=2026-02-08&children=0&infants=0&pets=0&source_impression_id=p3_1770217183_P35PuO2_GKDOvWhY&previous_page_section_name=1001&federated_search_id=ded4c80f-b22f-400e-8e87-2fe30186f859

[RRocket]

Who can afford $4k a week..let alone $9k a week.

We spend more than that for a weekend rental when we do our guys golf trips. Last 2 years our spring golf trip was just over $5k for 2 nights in an AirBNB, but when you divide that by 16 guys, it's cheaper than a hotel room for 2 nights. We usually end up in some pretty good places that sleep 16 comfortably where we're not stuck sharing beds, plus the last two we had waterfront properties, with indoor pools, hot tubs, sauna's.

It's more palatable when divided by 16.

I need to start renting my house out! Private beach, 5 bedrooms, sauna, on the Wine Route, etc

How much?? LOL 😆

[Blizzard]

Yep, if we went that route it would be in the Pensacola / Destin area and it's similar, right now you're looking at $4-6K/week to rent something similar, and that's typically what people do, couple families, or a larger family gathering. Places are booked solid April-November.

We go a couple times a year, and have a loyalty deal with one of the resorts down there that gets us a nice ocean view balcony room for about $2500/week....But it's just a room, not a house or even a condo. Which is part of my motivation here, if I am already spending ~$5K/year on rent down there, that would cover a good chunk of my operating cost if used some cash to buy a modest beach house that we could rent when not using it.

Course, there's risk....it's dependent on the vacation market, there's hurricanes to worry about, travel back and fourth when stuff goes wrong, etc. Plus, acquisition cost is relatively high. Locally here in the Memphis area you can find newer starter-home type detached properties for ~$200K, and they rent for $2.5-3K/month....While boring, the return on something like that, is pretty good, especially if you grab 3-4 of them. 

A few years ago we decided to buy an income property and thought seriously about a small house/cottage in the country to put on Airbnb, advertised as a quiet couples/solo retreat. At the time, there were some interesting houses going for around $250-300K, nothing fancy but cozy, chalet-feel, surrounded by nature, and some had access to small non-motorized lakes. We felt we could charge around $200-250 per night in our desired area. We checked out a few places but ultimately decided against for many reasons.

You used to be able to have a short-term rental anywhere you wanted but then municipalities started cracking down heavily on them with a bunch of rules like zones where they are/aren't allowed, there can't be more than X properties within a 1 km radius, you need permits, neighbour approval, etc... I totally get these rules because so many towns in cottage country have been invaded by partiers and people who don't care about nature and quiet, but it makes it pretty prohibitive to open a new STR. Either you have to buy a property that has a license already ($$$ + GST/QST), or hope you can get a permit for whatever you buy.

Then there's the issue of these smaller cottages being older and not necessarily built to code (expensive renovations and repairs - I'm not particularly handy other than basic maintenance and repairs, and helping out on a site with someone more experienced), having to manage the property from an hour away and potentially having to go there at a moment's notice if something goes wrong, and that 1% of renters who end up causing a ton of mess, damage, and headaches.

A lot of these latter issues could be solved by having a property manager, but the reality is that in these smaller country towns, there's a serious lack of reliable, hard-working labour that will take initiative to manage your property properly. From what I've heard, just finding someone to do a proper cleaning that goes beyond changing sheets and passing a mop, and having this person come reliably without flaking on you, is a challenge.

I feel like managing a vacation property can be a serious time drain and source of stress, and we really don't have room in our lives for that right now.

So ultimately, we ended up buying a rental condo in the city. Cap rates aren't great in the city, but we ended up buying a 1-bedroom condo in an 8-unit building built in 2010 that we now rent out in the $1,500/month range. It's incredibly boring and yields zero cash flow since our expenses and mortgage repayments take up the rent we collect, but after a quick rebab, it's been almost no work. We ended up lowering the rent a bit to secure an amazing tenant, and in 3.5 years we haven't had a single problem with the unit or the tenant. I spend maybe 20 minutes a month on admin/accounting work, and since I'm on the condo board, 1-2 meetings a year. The goal with the condo is to keep it until the mortgage is paid off in around 25 years, and then either sell/refinance and use the cash. The benefit with this kind of investment is leveraged investing... let's say you put 20% down, you can generate gains on a property worth $300K on just $60K of your money.

We've been thinking of buying another condo for the past little while but haven't found anything online that meets our criteria... most of what we've seen doesn't have a good purchase price-rent ratio, meaning we'd have negative cash flows each month unless we put more money down, which I don't want to do. Or they're in older buildings that do not have sufficient reserves, meaning condo fees have skyrocketed or past & future assessments, or have some fatal flaw like looking out directly at a brick wall, lol. The rental condo we own now is actually garden-level meaning half-basement, and we've found it's the sweet spot for a rental. The purchase prices seem to be 25% less than regular units, but rents are maybe 10-15% less. It takes more time to find a tenant obviously, but once they're there, the cash flows make sense.

[Blizzard]

Yep, if we went that route it would be in the Pensacola / Destin area and it's similar, right now you're looking at $4-6K/week to rent something similar, and that's typically what people do, couple families, or a larger family gathering. Places are booked solid April-November.

We go a couple times a year, and have a loyalty deal with one of the resorts down there that gets us a nice ocean view balcony room for about $2500/week....But it's just a room, not a house or even a condo. Which is part of my motivation here, if I am already spending ~$5K/year on rent down there, that would cover a good chunk of my operating cost if used some cash to buy a modest beach house that we could rent when not using it.

Course, there's risk....it's dependent on the vacation market, there's hurricanes to worry about, travel back and fourth when stuff goes wrong, etc. Plus, acquisition cost is relatively high. Locally here in the Memphis area you can find newer starter-home type detached properties for ~$200K, and they rent for $2.5-3K/month....While boring, the return on something like that, is pretty good, especially if you grab 3-4 of them. 

My aunt and uncle have had a place in Boca Raton, Florida since the 2000s, and the economics of owning there make it impossible to rent and make any money. They have a condo on the beach and while acquisition prices are semi-reasonable considering you're on the beach in a super desirable town (you can buy a decent beachfront condo there for around $1-1.2M USD), operating costs are INSANE. I'm talking insurance for your unit in the $5-8K range, property taxes of $20K and condo fees of $30-40K. Almost all buildings flat-out prohibit short-term rentals, so you're stuck with seasonal rentals only, and from what I hear you can rent for 3 months in the winter for around $25K USD. Even if you find seasonal rentals for the entire year (you probably won't), you're barely covering your operating costs let alone the acquisition costs. I guess it could make more sense with a single-family home, but 90% of Boca is HOAs and the areas that aren't are either sketch or start at $5M+...

[Blueprint]

Yep, if we went that route it would be in the Pensacola / Destin area and it's similar, right now you're looking at $4-6K/week to rent something similar, and that's typically what people do, couple families, or a larger family gathering. Places are booked solid April-November.

We go a couple times a year, and have a loyalty deal with one of the resorts down there that gets us a nice ocean view balcony room for about $2500/week....But it's just a room, not a house or even a condo. Which is part of my motivation here, if I am already spending ~$5K/year on rent down there, that would cover a good chunk of my operating cost if used some cash to buy a modest beach house that we could rent when not using it.

Course, there's risk....it's dependent on the vacation market, there's hurricanes to worry about, travel back and fourth when stuff goes wrong, etc. Plus, acquisition cost is relatively high. Locally here in the Memphis area you can find newer starter-home type detached properties for ~$200K, and they rent for $2.5-3K/month....While boring, the return on something like that, is pretty good, especially if you grab 3-4 of them. 

My aunt and uncle have had a place in Boca Raton, Florida since the 2000s, and the economics of owning there make it impossible to rent and make any money. They have a condo on the beach and while acquisition prices are semi-reasonable considering you're on the beach in a super desirable town (you can buy a decent beachfront condo there for around $1-1.2M USD), operating costs are INSANE. I'm talking insurance for your unit in the $5-8K range, property taxes of $20K and condo fees of $30-40K. Almost all buildings flat-out prohibit short-term rentals, so you're stuck with seasonal rentals only, and from what I hear you can rent for 3 months in the winter for around $25K USD. Even if you find seasonal rentals for the entire year (you probably won't), you're barely covering your operating costs let alone the acquisition costs. I guess it could make more sense with a single-family home, but 90% of Boca is HOAs and the areas that aren't are either sketch or start at $5M+...

There's been a massive property dump by snowbirds lately that flooded the FL market. Besides the politics (I've heard of anglo Canadians being evicted of a bar), the exchange rate makes living there just too expensive. A lot of Canucks now choose places like Mexico, Portugal or Spain.

[Johnnymac]

I've seen quite a few videos of people who have vending machines and contracts at locations that seem fairly profitable.  I probably would go that route if I was looking for a "side gig" for money.  Very little interaction with humans, minimal outlay of cash for initial investment, don't have to pay rent or utility bills.

Heck if I was as handy as Firm it would be a match made in heaven due to being able to repair and service the machines.  If I was as far south as him I probably would do a Canadian themed vending machine with snacks you can only get in Canada.

[Revelations]

Anyone invested in markets? (stocks, crypto) Holy $%&! What a bloodbath! Especially crypto. Everything is red and going down. Even metals are struggling to maintain a normal pace. I haven't seen this level of volatility in years. Looking at my portfolio is very depressing. 

[Firm]

I've seen quite a few videos of people who have vending machines and contracts at locations that seem fairly profitable.  I probably would go that route if I was looking for a "side gig" for money.  Very little interaction with humans, minimal outlay of cash for initial investment, don't have to pay rent or utility bills.

Heck if I was as handy as Firm it would be a match made in heaven due to being able to repair and service the machines.  If I was as far south as him I probably would do a Canadian themed vending machine with snacks you can only get in Canada.

The vending machine thing isn't a bad idea, I like the Canada themed thought...iunno if it would fly, but it's pretty creative, lots of good Canadian snacks that don't exist here. I think you'd lose quite a bit in damage/theft though...places that allow vending machines around here tend to be on the rough side.

[Firm]

Yep, if we went that route it would be in the Pensacola / Destin area and it's similar, right now you're looking at $4-6K/week to rent something similar, and that's typically what people do, couple families, or a larger family gathering. Places are booked solid April-November.

We go a couple times a year, and have a loyalty deal with one of the resorts down there that gets us a nice ocean view balcony room for about $2500/week....But it's just a room, not a house or even a condo. Which is part of my motivation here, if I am already spending ~$5K/year on rent down there, that would cover a good chunk of my operating cost if used some cash to buy a modest beach house that we could rent when not using it.

Course, there's risk....it's dependent on the vacation market, there's hurricanes to worry about, travel back and fourth when stuff goes wrong, etc. Plus, acquisition cost is relatively high. Locally here in the Memphis area you can find newer starter-home type detached properties for ~$200K, and they rent for $2.5-3K/month....While boring, the return on something like that, is pretty good, especially if you grab 3-4 of them. 

My aunt and uncle have had a place in Boca Raton, Florida since the 2000s, and the economics of owning there make it impossible to rent and make any money. They have a condo on the beach and while acquisition prices are semi-reasonable considering you're on the beach in a super desirable town (you can buy a decent beachfront condo there for around $1-1.2M USD), operating costs are INSANE. I'm talking insurance for your unit in the $5-8K range, property taxes of $20K and condo fees of $30-40K. Almost all buildings flat-out prohibit short-term rentals, so you're stuck with seasonal rentals only, and from what I hear you can rent for 3 months in the winter for around $25K USD. Even if you find seasonal rentals for the entire year (you probably won't), you're barely covering your operating costs let alone the acquisition costs. I guess it could make more sense with a single-family home, but 90% of Boca is HOAs and the areas that aren't are either sketch or start at $5M+...

There's been a massive property dump by snowbirds lately that flooded the FL market. Besides the politics (I've heard of anglo Canadians being evicted of a bar), the exchange rate makes living there just too expensive. A lot of Canucks now choose places like Mexico, Portugal or Spain.

I think this is blown out of proportion a bit....I literally spend 100% of my time in the US, and travel to different cities usually once a month and never have I ever felt unwelcome or discriminated.
Now, if you're in a bar and you're mouthing off about how much better Canada is, yeah, you'll probably find some trouble. But the same would be true of an American in a Canadian bar.