Here in Florida, attorney's fees are statutorily recoverable in all residential tenancies and even seemingly minor noncompliance by a landlord can produce a dismissal of their eviction and a judgment for fees against them, despite a non-paying tenant residing in a rental.This is not legal advice and does not create an attorney client relationship.

From our conversations the seller seems to be comfortable with his buildings producing.

It would be nice to buy a deal like this for what it was truly producing, but the reality is the rental market is just too good right now in this area of Chicago.

But definitely interesting the added income diversification that an Airbnb rental might produce.

Third, the government takes, takes, takes from the producers like my parents and gives to the moochers.

I've read mostly positive things about using a HELOC to invest in income-producing properties, although I've also read that it's a good idea to hang onto it for emergencies. 

I suspect this may vary from person to person, but my experience has been that real estate brokers tend to be upstream of a lot of business so the folks that are downstream tend to want to meet with producing real estate agents to see if they can be on the receiving end of the down stream business.

They don't want to sell at a discount, and they're willing to hold onto it until it can either produce cash flow or sold at retail. 

Historically San Diego RE investing has produced outstanding ROI.  

Cash deals produce more money when the deal is said and done but leveraged deals create more ROI.