Tourism keeps short-term rentals booked, while long-term rentals offer solid returns at a lower price point with steady demand.

Can't beat the cash flow from a paid-off rental!

I owned a rental in 2015 but sold it to make a big move to Florida.

We’re debating whether we should sell our rental property to pay off all our debts.

Another thing to add is the regulations, HOAs and Cities are imposing a lot of regulation on short-term rentals or rent by a room, I have seen some HOAs regulate the amount of people authorized to rent the property too.It requires to do a lot of due dilligence to begin with mainly in such big house. 

If I were in your position, I would buy a duplex that has potential for value add, fix it up, live in one unit and rent out the other unit as a medium term rental or long term rental.

Investment Info:
Single-family residence buy & hold investment.

Purchase price: $305,000

Cash invested: $80,000

Single Family home in a 55+ community. 2 Bed 2 Bath, attached 2 Car Garage. Tile ...

The people who struggle here usually underestimate those factors.One thing I do differently than most: I share actual performance data from my rentals—purchase prices, rehab details, rent numbers, lessons learned, and backstories.

My problem i is my market is super expensive if I stay in the nyc area and I don’t have the confidence since I don’t have any actual experience to invest out of state do you guys think paying off my mortgage would be more beneficial than looking for more rentals .

That likely means that they are not good with money management which you are likely expecting from him.To answer your question, if you are doing long-term rentals, the LLC taxed as a partnership is likely the go to route.Best of luck.