I am hoping this post will help those interested in the BRRRR investment strategy avoid this common trap. From what I consistently observe, the ability to complete the BRRRR investment strategy and recapitalize onesel...

Get with a Chicago-based real estate attorney that understands the RTLO and see if you fall under any of the exclusions.

The LTR rents are pathetic compared to current values, but maybe if STRs get banned the prices would fall.  

Ugh, tiny houses fall into this tiny crack where they are disqualified from pretty much everything.

Last fall I put offers in on some properties in Grass Valley and Nevada City at prices that would at least break even on initial cash flow, but sellers still thought it was Q1 '22 and would rather take their properties off market than sell for less than what they considered them worth. 

Our last vacancy actually took weeks longer to rent out than expected, but it was late summer/fall and it was advertised significantly higher than previous long-term tenant had been paying.   

Also, if the groups that you are investing with offer any type of tiered structure, are you typically pooling enough capital to fall into a higher tier?  

In other words, if it were to fail, there is no fall back. 

The problem is taking them collectively results in new problems for our lot...the three solutions work when you look at just one of our shared lines, but when you look at all three the math falls apart...my surveyor will have to take their collective work, his new field investigation and then apply his own good theories, and hopefully our property is the missing piece in the puzzle for how to resolve this.I share that because those three surveyors are all names I or my boss know, and do good work.

Change your mindset from that of a victim to that of the investor and look for the solution.