They actually owe more than they can sell it for.

It's a more affordable market and lower property taxes, so you may actually have a chance to cash flow.

Of those 10, 5 will need long term follow up, 3 will be tire kickers, and 2 will have actual immediate interest but only 1 will pull a trigger. 

I figure if the equity we have cash flows better than similar equity in a single family residence in Utah would, then we should consider this AITD as a serious option.

I would go with option A.

In addition to what was said above, for the software that has a free trial option, sign up for it and use the software for a day (or at least a few hours) as if you are using it for real, then call their customer support too and get a feel for that. 

@Dana Yobst While it may seem like a simple concept, it's actually a very complex process that requires significant documentation as well as specific methodologies.

Does a cost seg or bonus depreciation actually help you in any way? 

Our company is actually starting an Asset Management Mastermind to address these infrastructure issues and share our systems and procedures.

The increasing barrier to entry results in fewer new STR's coming available for sale, but also fewer options for guests to rent.