If anyone has any recommendations of groups/individuals who share that common interest, I would be much obliged.

Sometimes a note is added or a specific permit condition is added that will prohibit a use otherwise allowed within the zone...it's not common and probably less common out your way where entitlements are more reasonable, but still could be something to check.

If you have service issues (common enough, from the time I’ve spend in L&T Court), it can take 4-5 months.

I have seen certain streets in Milwaukee where most of the houses don't have basements and in those cases, it's not as great of a concern for me but that's not a common scenario. 

This 2x LLC structure with some umbrella insurance is quite common and gives most people all the legal protection you would need as a real estate investor.

Craigslist is a common place people search for small commercial spaces.

Just educate yourself on the model and common practice.

These kinds of loans are common, but there are a few things to keep in mind.

Is this common for the principal amount to increase this dramatically?

Seller financing is actually very common, and there's tons of info here on Bigger Pockets about it.