My preferred market is Columbia, SC. 

You can easily get a ballpark on what insurance would be (more expensive for multifamily) by asking for a couple estimates or talking to a broker.

Over the past year or so, I have seen a couple of smaller commercial buildings come on the market that seem to be at tempting price points - 415 N Michigan (listed for $199,000) is a current example.   

@Kayla PrangeI have a couple of STRs for a few years and more experience with my LTRs.My short term rentals are much more unpredictable compared to my long-term rentals.

Figure out what kind of property you prefer to start house hacking with single family, 2-4 units?

I've found a couple of interesting flip opportunities but I'm not sure I want to take it on my own or if they are as nice as they look on paper.With that said, anyone south of Nashville TN doing flips/rehabs and interested in chatting?

But if you are talking decent sized towns with more than a couple major employer, you are likely to be fine with smallish properties.  

Seems like a doable thing to me.Like @Noah Corwick mentioned, you need to make sure you account for your time there, but when you say use it, do you mean for a couple of months or a week here and there?

So with the garage conversion, he thought there might possibly be a way to convert the garage to a couple units, but still somehow classify my property as "residential".   

The GPs don't seem to know each other all that well maybe like just for a couple years.