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. 

Be sure to: call & verify employment references, request pay stubs to confirm income & check rental history by contacting the previous landlords.Keep the momentum going!

I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.

Who pays when the resident breaks the agreement and quits paying? 

One would think that a bidder would pay $45,000 in my example (since they are assuming the first mortgage), but they are actually bidding $225,000.

@Jon D. some questions, the answers may help you better focus.1) Why did you pay your primary mortgage off in the first place?

If not, who do you believe the natural buyer is and why do you believe they will pay retail when they can replicate what you accomplished with any number of available properties on the market at any given time?

So all of the gain and depreciation recapture are initially still tax deferred.However, like Joe said, the down side is later when sold  you lose the 1031 option. the client will pay tax on all gain and depreciation recaptured from before the 1031 also. 

I reduced my responsibility to only taxes/insurance while the tenant buyer does the maintenance, pays utilities and makes monthly payments to me. 

I’ve had people who signed up for 6 months and stayed 5+ years, paying increasing rental rates.