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. 

Hi,I am a new member to Bigger Pockets and have several rentals around Algonquin,IL. 

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.

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.

So far, my experience from interviewing several companies in that town is that most of them completely refuse to manage furnished rental.

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.  

I previously owned rental property but sold them and am now looking to get back into real estate investing.

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 .

It’s crucial to ensure that your cash reserves can cover not only the mortgage but also unexpected expenses during the remodel.The 30% housing rule is a helpful guideline to avoid overextending yourself, and ideally, you should be comfortable with your monthly housing costs even without rental income.