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Vacation property, how to do it right?

I wouldn't go down the route of renting your boat out. Too much to go wrong. Let them rent from a marina.

I would hire someone to do the cleaning. The vacation rentals that I have used are cleaned by someone (not the owner). You don't want to obligate yourself to running down there every time someone checks out. Find a semi-retired cleaning lady or Mexican.
 
Ha. I've seen a few of these places make the renter clean after. But I think that's very rare.

There's a ton of things to consider with this, and renting 52 times a year will always be more of a hassle than renting an apartment for a year. But there's no way I can't get double renting this house than renting out an apartment where I live. Heck it might even be 4x

@Willy4UK Love your Orlando idea BTW, but I'm 2,000 miles north.
 
A boat is NOT an investment, it is a luxury expense. Or it's a giant hole in the water you throw money into while trying to have fun.

I wouldn't rent mine out. Read your insurance carefully, most of them won't allow it or will charge you a hefty fee if they do allow it.
 
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Ha. I've seen a few of these places make the renter clean after. But I think that's very rare.

There's a ton of things to consider with this, and renting 52 times a year will always be more of a hassle than renting an apartment for a year. But there's no way I can't get double renting this house than renting out an apartment where I live. Heck it might even be 4x

@Willy4UK Love your Orlando idea BTW, but I'm 2,000 miles north.


Dude, say you're moving here as your primary residence. My mortgage payment is $630 plus $250 HOA (actually HOA fee decreased last year). It literally it takes 5 minutes to get to the first gate of Disney World. Whoever I bought my condo off of was someone who used it as an Air bnb. Like I said. Plus you can come down and get drunk on occasions. Prolly hook up and murder some prostitutes. (edit-jk)
 
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Invest your first $10k in an index fund, your next $10k-$20k in a permanent residence then have some fun. Don't be in a hurry just because some rich kid has a Beemer in his driveway and his Dad's beach house whenever he wants it.
 
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I'm serious about this condo place over here. Dude. I'm basically on Disney property. These places are 24/7 rented by Disney employees. This place is .25 miles from the only 6th star hotel in Orlando (Gaylord Palms).

$100K or cheaper (not getting a 1/1 under $90K). Silly to throw money in a lincoln log house. $250K? Ridiculous.
[laughing]
 
Dude, say you're moving here as your primary residence. My mortgage payment is $630 plus $250 HOA (actually HOA fee decreased last year). It literally it takes 5 minutes to get to the first gate of Disney World. Whoever I bought my condo off of was someone who used it as an Air bnb. Like I said. Plus you can come down and get drunk on occasions. Prolly hook up and murder some prostitutes. (edit-jk)
STOP, I'm dying here Willy! [laughing]
 
Invest your first $10k in an index fund, your next $10k-$20k in a permanent residence then have some fun. Don't be in a hurry just because some rich kid has a Beemer in his driveway and his Dad's beach house whenever he wants it.

But but but.. I want the Beemer and beach house!

My 401k is strong right now, opening up my Roth IRA through Vanguard with the first $1000 I save, which will be next week (not going to pull from my savings accounts). I'd like to max it out at $5,500 a year.. but that might be a bit too much.

Sounds like I should buy the Duplex first. I wouldn't go in on this lake house alone. I think I'd only go halves with my Father, where I pay an auto-like payment to own half, maybe even a small DP to help him out, and then start collecting on vacation rent. The house/property is 250k, started at 600k, and lake values are only going up.

IF I go halves on the vacation property, I could still swing a duplex, maybe just a year later than expected. I really think the returns and worth of this vacation property are solid.
 
Owning and living in a duplex as a young single male who's fairly handy while renting out the other half is the best financial decision I've made to this date.

Had someone else paying the mortgage while passing through a nice little tax loss at the time. Deducted half my otherwise nondeductible insurance and expenses related to the property.

With Zillow now, it's incredibly easy to list your property for rent. There are services for rental applications that easily do credit, criminal background and eviction history checks.

However, I haven't bought a boat and vacation home with a crumbling foundation yet to compare the returns.
 
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I more meant extended family, not so much nuclear family. If extended family wants to get pissy, they can look at my two younger brothers.. they won't have to pay any money for this like I did. Which I'm fine with, personally.. they are 1 and 3 years old.. I'm 29.

My relationship with my brothers is pretty unique, I could be their dad, and more or less will be a "dad" figure to them. As long as I retain 50% and "voter rights" I'm fine.

But it's still a good point. Maybe they grow up to be shitbags and I'm stuck splitting a house with them they don't take care of. There could definitely be issues.
 
Owning and living in a duplex as a young single male who's fairly handy while renting out the other half is the best financial decision I've made to this date.

Had someone else paying the mortgage while passing through a nice little tax loss at the time. Deducted half my otherwise nondeductible insurance and expenses related to the property.

With Zillow now, it's incredibly easy to list your property for rent. There are services for rental applications that easily do credit, criminal background and eviction history checks.

However, I haven't bought a boat and vacation home with a crumbling foundation yet to compare the returns.

Trust me, that is still the goal, and has been since I graduated. But property values are high in New York and so are the taxes. I'd imagine New York is one of the states that is better to rent than buy.

And FWIW, a Duplex that's in good shape, in the area I want, starts at 200k. The vacation house is 250k.

New York is a real whore...
 
"Doing it right" would be buying a sweet timeshare in beautiful Myrtle Beach, South Carolina.
 
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