do those things sound like deal breakers?

So if I wait till the market goes up then I will be loosing 12K per year on the smaller house that I am trying to buy to replace the big one

It's not a fully amortized loan, but rather a simple interest HELOC, which sounds like what you're looking for.

I don't think you can split up a 1031 across multiple properties but, it sounds possible.

Does this sound crazy? 

I know this sounds unreal, but I swear, every word is solid gold true. 

I'd be interested in a Chicago Discord group sounds like cool software and a way to connect.

Sounds exaggerated?

I don't know how realistic this is but it sounds pretty good, if you're in the right location, with the right management.

.- Property now rented for $1000 per mth- Current Value Estimates: Redfin - $114K, Trulia - $113K, Zillow: $113K; still doing research on comps because the area is hit and miss so last I saw was a projected $100K***************************************************************************************************************************- Navy Federal Credit Union say they can do 65% of original purchase price in cash out refinance - $34K- Hard-money lender offered $30K at 9.9% for 6 months as rehab loan, which I'd use to replace roof, windows, doors, and cutdown at few trees;  then cashout refi for 50% of the appraised value between 6 and 9 % depending on personal credit.