So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

Explore my personal favorites, Set For Life by Scott Trench or The Total Money Makeover by Dave Ramsey, for invaluable financial insights.3.

If you need more to do the rehab, perhaps instead of partnering, you could get your former boss to do a personal loan. 

I 100% agree with the intent aspect and that is an important premise, but the fact is in this particular situation intent for it to be personal use has been confirmed (by way of a public post).

The person leaving the trailer there is just to store it there.

I have read all of the "trends" and statistics but now I am Looking for feedback on personal experience in the Akron market.I appreciate it! 

If not from the person in office, then definitely from the person running against them.

This person did not raise any money, they invested around $600,000 into the offering and because they were one of the larger investors were considered a Co-GP because it was a new sponsor and they needed this persons $.

Just my personal opinion - get a mentor or a person who already has good experience running STR business, preferably in your area (but not 100% required). 

I personally like Alabama and Tennessee a lot, depending on what specific area you're looking at.Look for Class B or C properties in stable rental markets, particularly single-family homes or duplexes.