I will preface this with the fact that I have a legal background, specifically with estate planning and asset protection.

Yes, they are getting higher than market rent for that specific Neighborhood, but they also have a hard time finding a S8 tenant that wants to move into and stay in that Neighborhood.

Selling your share at fair market value could avoid gift tax but may trigger capital gains tax for you based on the sale price and your cost basis.In California, the transfer may also trigger a property tax reassessment under Proposition 13 unless a specific exemption applies.

Zillow is not ideal because this is a monthly furnished rental - which Zillow doesn't have a specific platform for - but that's what has worked for me up to now. 

However, I agree with you that I will never again work with that specific attorney again.

While podcasts, books, seminars, and websites offer general knowledge, you'll buy a specific property in a specific location, subject to local rules and regulations.

They specifically specialize in group vacations, so kind of similar, and no doubt have spent a ton of money analyzing and figuring out what works. 

Here are a few additional strategies that might help mitigate risk if you decide to rent the property:Hire a Strong Property Management Company: While you’ve already spoken with some PMs, consider finding one with extensive experience managing single-family rentals in Cook County specifically.

@Ashish AcharyaYou're merely reproducing the IRS position, the one I specifically challenged.

My feedback is specific to REI vs what they marketed to me thus far (as I said 1st property with them).