@Kyle Kulhanek To retitle your Chicago condo into an LLC for liability protection, start by forming the LLC with a clear operating agreement outlining ownership and responsibilities.

Those who just try to copy the price model and not the operational leg, yeah they don't last long. 

The cash investor who "saw the property on zillow" but doesn't really understand what REO means or how the banks operate. 

I was just on their website looking at the permit process:CityofSac-STR PermitLooks like 90 days max until you get a conditional use permit but still reading as it seems a little unclear:A short-term vacation rental may operate from a location that is not the operator's primary residence for a total of 90 days in a calendar year.

I understand that they operate in real estate under one of a few exemptions from registering as a security with the SEC.

Depends on the operating agreement and docs you signed.

@Ella Marie, I can't speak on behalf of your market, but in my respective market, competition is tough, and the successful fix-and-flip vendors are often full-time operating businesses.

In the six years I've owned, operated and sold vacation rentals on the Oregon Coast the investment landscape has evolved considerably. 

We actually CAN'T explain what we are seeing if we are operating on the "purely rational actor" hypothesis (as you implicitly observe), we MUST include highly irrational and emotional individuals to explain what we are seeing.- Investor uncertainty.

This is anecdotal information based upon the interviews I’ve had with operators across the country.