Yet your contractor will just ignore it and not even put it in budget and it will come up later.When I weigh the risk and rewards of flipping right now, it's not even close. 

I'm not the reason why the cops are ignoring the criminals next to your building. 

I have been guilty myself in the past of ignoring or minimizing red flags that would have saved me a lot of trouble later just to get a vacancy resolved.

Concentrating on a single source of the RE return is ignoring data that largely dictates the total return.When starting out you may need cash flow to pay the expenses.  

@Chaim MalIn my personal opinion, you were sold snake oil and you want to buy even more of it (trusts).Cut your losses by dissolving (or at least ignoring) these unnecessary structures and close on your property under your personal name.

Even though the requirements are listed in the ad for the property, prospects tend to ignore them in the add.

Excuse my ignorance @Jodi Taylor but what is a Chicago discord group?

Whatever the case, I'd say you're wrong on this one for sure and the OP should ignore any advice you give - at least on this thread/operator.

Ignore the responses that are not from local investors, in Chicago an eviction takes 8+ months so you should NEVER take on any risky tenants.

Ignoring the new law, you should always try to structure your personal use so that you would avoid the vacation rules.