Intentional, with forethought, planned, designed and anticipated. 

I would also target COA’s with newly replaced roofs, and negotiate to have the seller pay any outstanding special assessments at closing.

I'm curious with already-in-place commercial tenants, besides checking that they are paying on time, is there any other due diligence you do on the tenants before purchase?

I don't have large money to pay off the that lien.

Definitely not an exhaustive list, but those are trades that I'll waste tons of time on and likely do subpar work when I can pay a pro who will do it in 10% of the time and the labor costs are pretty reasonable. 

The issue is less about piercing the veil, and more about giving the insurance company an excuse not to pay out because the LLC is not the primary covered.

I'd say yes, you pay for it in the rate though. 

Have you decided on a target market that you plan on investing in yet?

A super ball number to get you going would be at least $190/SF-$220/sf ish... to figure out square footage it's probably best to connect with a Chicago architect like @Samuel Pavlovcik or @Prashanth Mahakali both can talk through the zoning and plan development process.

Your refinance loan amount isn't enough to pay off your initial financing.