I tend to shy away from homes over ~20 years old to buy and hold for long term renting.

But by building a successful short term rental business on someone else’s property aren’t you giving away the increase in value of the property resulting from your efforts to the property owner?  

Purchase price: $320,000 Currently have a long term renter, the rent pays the mortgage and other expenses but provides no cash flow.

Quote from @Elam Fisher Jr: Anyone have experience with mid term rentals in Baltimore city?  

Just a few hours of preparation could have saved you many hours of effort, a lot of worry, and thousands in lost income.

Avery Carl's Book, 'Short-term rental, long-term wealth' How did you find this deal and how did you negotiate it?

Negotiating favorable terms is both an art and a science, and in real estate, it's a critical skill that can make or break a deal.

Are you looking to flip or for long term?

I agree that the best way to make money is self manage your short term rental (not AirBNB, that is a platform).

I've done it twice in Reno, NV (now I have them both as long term rentals), and it's changed my life.