My advice would be, if you truly want to learn the business, lease it up, refinance, pull some money out, and go on to the next one.

But you do have to put some language in your lease  agreement or lease addendum that deals specifically with issues that will come up for the fireplace.  

We're also able to evaluate our rates, and keep pace with inflation, on a monthly and quarterly basis because of shorter term leases.

Your PM will be able to help you manage everything from leasing, regular maintenance to bigger ticket items like replacing your roof and managing tenants.

What started off as primarily a second home with the possibility of short term leasing quickly flipped to a STR first and a second home when not rented because demand is so strong right now for STR's in this area. 

I don't use padsplit (weekly rentals); I rent on long-term leases in B Class neighborhoods.

I receive emails from them frequently, but I have not had time to really go back and try it again. 

A furnished mid-term rental or month to month lease can be well worth the small incremental monthly cost for this flexibility if you are serious about finding a great live in flip candidate on your timeline, not that of your employer's. 

In those cases, the main criteria we add to our lease is that everyone that comes to stay there must be subject to a background check paid by the company.

For example, what would the cash flow be like after you renovate and lease out at the new rates?