I'm curious if this has come up with anyone else and what I can do to help the seller in the situation to get the deal?

I am in a very similar situation  @Chris Scarazzini just starting out!

You are right about the risk that comes with the holding period but in my opinion sometimes you have to take the risk and make sure the profit that you generate is higher than the costs that you paid by holding the deal for a specific amount of time.

@Alex V. you've got some good responses above but this specific forum is more for residential stuff. 

@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.

You will want to talk to a CPA to see which hours count and which hours don't as there is a lot of gray area with your situation. 

Cities don't play fair when they decide to go after you.One thing I would also suggest you do is look on AirBnB for the specific building you want to buy in. 

I’ve been in your situation and have had to call dozens of banks before I found one that gave me what I needed.

But I did not want to give specific examples with no context on a location for her. 

Watched some You tube videos about some ways, specifically creating a property LLC with WY LLC being a member manager LLC for the property LLC.