Just want to make sure the folks running this are not buying helicopters and jet planes with our investment.Comments welcome.   

This would be from the same carpet company I used when I fixed up the house, so not trying to gouge them or anything.I'm looking for some guidance in this situation, pitfalls I could run into, or just straight up illegality.

Seems interesting run a split test see if it works out for you.

What are the largest pitfalls one may run into that turn this from a 150 to 350 ordeal?

I still want to have a “regular” career for now, but know I have what it takes to successfully run a business- say in the form of real estate investing.

They stopped paying the lender and wanted to work something out with the lender but the time is running out (ie the management company did not do any significant improvement during the forbearance period) One of the LP just emailed me and said we need to raise 65k to enlist help from this company.

But my realtor said they are going to do special assessment on this property and HOA runs badly. ( We requested HOA reserve document but no answers. ) We wanted to wait to see how special assessment going and close. 

Given that I'm not positioned to buy just yet, and simply running the numbers, is there a rule of thumb for estimating insurance costs that would make sense in Cook County?

It’s a gem for insights into running and expanding a business.

If I may, a lot of the issues we are running into with insurance is that consumers no longer use insurance as a catastrophic fall back but rather, they nickel and dime on small claims that compund into larger issues.