If you do outsource, some management companies will cover various things like cleaning, supplies, etc. so look into that as well. 

As to others points rents will change with supply conditions.

we invest in non performing mortgages (and do some short term RTL's), and the indicators we look at are our inventory supply and where is the inventory.

Because of this the supply is relatively low which means the ones that do exist tend to make good money, especially if you theme it toward bachelor/bachelorette parties.

@Ashish Acharya A big part of my post is highlighting how specific details in local regulations can make it increasingly challenging to operate short-term rentals, even in towns where they’re technically permitted.

Selling a property that requires significant work can indeed be challenging, but there are several avenues you might consider exploring:Local Real Estate Agents: A local agent with experience in selling fixer-upper properties or historical homes in your area could provide valuable insights.

If its easy and been easy for a long time, you haven't challenged yourself.

Challenges?

We will meet at different adaptive reuse location each meeting to see the transformation and discuss the opportunities, challenges, and rewards of this strategy.

Basically, the demand is much weaker than the supply.