Fannie Mae will allow you to transfer the deed to an LLC if you decide to try to go the conventional route, but the loan would still be in your names and you'll need to pay a title company a second time post-closing to do this  for you. 3) I can't speak for the area so no comment there4) If you're self managing, make sure you find vendors you can trust in the area since you won't be able to easily verify if an HVAC guy, plumber, etc. is trying to rip you off and tell you to buy something you don't actually need. 5) Make sure you have clear alignment of goals and a clear operating agreement that spells out what to do if those goals start to not align in the future since you'll be jointly obligated to these properties. 

one thing I didn't see in this thread is... do you WANT to own and operate an STR?! 

And I also realized that we would have to re-tool our operations, which are 100% specialized to the type of property we have.So you don't have to go bigger, unless you want to.

You are effectively operating a hotel, which is a business enterprise with very different risks and hazards to insure.  

If it's currently an STR they should be able to provide you with the p/l statement from prior years so you can see gross rents, operating expenses, average daily rates and occupancy levels.

I will say that even though you get the boost from VRBO and AirBNB, the first year of operation is usually lean as you build up the rep.Offering a discount on the stay is a way to be more attractive but don't go crazy.

Airbnb operates as an interest-based algorithm, rewarding listings that grab attention and keep potential guests clicking.

I’m in Ohio, so I can purchase a property with $40k cash out, invest $10k in repairs, and rent for a couple hundred above the monthly operating costs.

Congratulations on the duplex -My investor clients have acquired several multi-family investment properties locally in the market I operate in Northwest Indiana - Figure out your personal investment objective for the next 4 years and align yourself with the next property that make sense in this current market environment-

Board collected those funds and put them in Operating instead of Reserves.