I can't see how they can tell if days were blocked for personal use or a rental.

If your chances of saving your a…. by simply having each property in a LLC rather than personally is small, say 1 out of 200.  

If Jefferson Park looks mediocre in person, I’d keep looking rather than settling for West Town just because it’s the “sexier” neighborhood.

One of them he paid my personal residence mortgage for the past few years.

Personally, I’d focus on what’s tried and true in the area, especially if you’re keeping a close eye on the budget.Hope that helps, and excited to hear what you end up doing with the space!

For personal homes if it adds to your  personal comfort, do it. 

I find that when people know that their partner has a face, they tend to be more accountable because any recourse event would feel more personal.

And via not taking advantage of the next person, but via giving the right person an "in" they've maybe not readily found. 

The customer service person sent me a receipt to show they gave me a refund.

Do you ever network LOCALLY, in real life, in person, form local trust relationships and get personal recommendations and referrals?