I imagine I can get his wages garnished or maybe collect from his tax return.  

Before you close, can the rent from your buddy and the midterm tenant cover your mortgage, taxes, insurance, plus a bit extra?

To make a new property cash flow with current prices, interest rates, taxes, and insurance, you're putting at least 40-50% down.

The worst experience we've had was with a flat roofer (very common roof type in Chicago) we finally wrapped up, after waiting almost two years for them to finish/fix something. 

The foundation was already approved, permitted and finaled years ago for a 3400 sf house, and its solid and I won't be building directly on the overhang edge; but rather back away from the edge a few feet to prevent any load issues all the weight will be on the longer sides of the existing footing.

Finally, The rent control discourages further development, limiting supply which results in higher rents.So rents go up, but the rent control advocates are too uneducated on the economics of the rent control policy to see their role in the rent increase.Another consequence of rent control is no value in keeping the property as nice.

Immediately, I performed a Roth conversion, and instead of paying taxes on $50K I'm paying taxes only on $21K.

The only part that Property 1 pays on that loan is the escrow for property tax & insurance for Property 1.Thank you for your insight.You need to look at purchase price to determine cost basis, not how you financed the purchase.

Since they're low income/tax credit, they just don't make the kind of money needed to pay those huge premiums.

Start small and aim for properties that cash flow well, even after accounting for taxes, insurance, and repairs.Most importantly, keep taking action!