I'd consider doing some kind of cash out refi on the property at a number you're both comfortable pulling out, while still leaving $ for reserves to maintain the STR you currently have.

Well it all depends, it's all in what kind of business a person want's to shape.

You are questioning the value, unsure what kind of buyer would be interested, etc?

What kinds of changes are you looking for to NOT renew an existing tenant?

Typically interest only, construction bridge loans are great for that kind of transaction. 

I wish I had this kind of venue when I was coming up in the game.

I'm also considering a separate living room space or maybe some kind of artist studio. 

If more important items such as plumbing, electric or mechanicals are not working we will also address that for them but typically we avoid those kinds of properties if its to extensive.For those who are familiar with wholesaling you fully understand that to wholesale none of what we just mentioned above is necessary or obligated to be done in order to wholesale.

But it won’t take that kind of event for someone who needs cash flow to fail.

It is obviously for a different reason but the idea is same either what kind of business you are in.