Quote from @Ben Russell: Although I agree the leases and the legal implications of "Mid-Term" rentals and "long-term" rentals are closly related, I don't think the leases should be identical. 

Beyond that it's not in my nature to complain; I just like to identify problems and solve them, and if I can't solve them then either accept them or move to greener pastures.  

It’s great to be trusted with others hard earned capital but I only accept that responsibility because I KNOW I can do the job - that I have done the job over the years. 

If you pay more, you won't meet your metrics and will probably have negative cashflow and/or equity.You may have to make 10, 20 or even 100 offers to get one accepted at the price that meets your numbers.This is what all investors did BEFORE the Great Real Estate Crash of 2008-2010.

Curious how this will play out in the courts (granted it's LTR) and affect pricing products used for STR such as PriceLabs (which I use but have to seriously manually adjust for very specific reasons). I'm aware that ...

Hopefully your tenant accepts responsibility.  

@Thomas Farrell if you have any experience managing property/construction projects, I would look in to flipping properties and keeping the once that you see an acceptable cashflow on when finished.

I added arcade games, board games and accept pets as well.

My idea to achieve this is to convert the studio into a short-term rental.I’m trying to determine if I’m forcing this deal to work by relying on the short-term rental strategy or if it’s a reasonable approach given the numbers.

For this deal to work under those conditions, the purchase price would need to be closer to $179k.With your original assumptions 249k, the deal is marginally acceptable but not great, given the negative cash flow in the early years.