Coined the name "Short term rental loophole" which can provide massive tax savings for you, unfortunately the federal tax code establishes stringent criteria, including guest stays limited to seven days on average and the provision of basic hotel-like services, to qualify for this advantageous tax treatment. 

I've only heard this recently in a book I read, and by a closing agent from a title company.

Last but not least, would hiring a commercial leasing agent specializing in retail be the best route and would they help source potential clients?

I'd first have an agent send comps so you can have a good idea on the value then just weigh the options, run #'s and do it

First CommonwealthFirst Midwest, up to 90% Chicago areaFirst Tech Federal.

I can't speak as to the quality of the staff or agents where you live, but I can tell you that if you're not satisfied with whoever you get assigned, you can ask for someone else.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

The most mind blowing ones are where agents bring deals to sell off market.  

If you want to "sling deals" get licensed and become an agent, or consider getting into wholesaling.

We were in contact with a Redfin agent who also has a STR in the same building and gave us addresses that allows STR in Honolulu.