Hope someone expert in Real Estate can guide me1)Who act like qualified intermediary?

They can evaluate your specific case and guide you through the process effectively

If you end up in Cleveland you'll want to read The Ultimate Guide to Grading Cleveland Neighborhoods to give yourself an in depth idea of the market.

A good way to get an understanding of how to get into STR is :STRATEGY: Start Up Guide to Short Term Rental Investing 

Table 1-4 is the Rollover Chart in IRS Publication 590 that can guide you.

True investors, that are personally guided, can get good results.

As for your specific scenario, I would encourage you to reach out to a professional to guide your tax planning activities ASAP.  

I think this will help to guide you down the right path. 

Then let them guide you, play devil's advocate and act as the borrower, and cover your blind spots.

Pretty much the core of the STR business.Higher your rank gets, you can increase your price and be more picky in selecting customers which usually lead to a better review / less party or complaints / less expense and higher profit with a happy life.I know some people will argue, but the ranking system is the truth and should be the only guide to your STR journey.