Even when talking with some real estate professionals who would seem to have an incentive to help me with renting out my property, I have been met with serious warnings (they pretty much say don't do it).

Here is a newly created resource on BiggerPockets, which touches out cost segregation, accelerated depreciation, bonus depreciation, depreciation recapture, Real Estate Professional Status (REPS), STR Loophole / STR Strategy, example properties, and more. 

Absolutely - East Hill is a really popular area for traveling heath care professionals, as well as military on short term TDY orders who are looking for furnished stays.Keys to success for my condo have been keeping the furniture fresh, and not looking like every other listing out there.

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

If you're a relatively new multifamily operator, you'll likely be required to hire a professional management company (inexperienced owners are typically not allowed to self manage the assets).

Readers should seek professional advice.

It is right on the fringe of being legal/illegal, and lawmakers have been talking about how to regulate it for years because it can be a dangerous process that leaves end Buyers feeling like they weren't represented.....especially when they see the closing statement and find out how much the wholesaler made just by getting to the Seller first. 

Whether it applies or not it's always a good idea to check with a professional first so thanks for the reply.

Here is a newly created resource on BiggerPockets, which touches out cost segregation, accelerated depreciation, bonus depreciation, depreciation recapture, Real Estate Professional Status (REPS), STR Loophole / STR Strategy, example properties, and more.Cost Segregation 101 Author: Sean GrahamHappy to answer questions :)

If you know of any exceptional professionals in the Cleveland area with a strong track record or if you believe you are one yourself please reach out to me and I will get back to you.