how do I determine which market to begin my real estate investing strategy - seeking small multi family units with positive cash flow of $100/unit of more

If you lived in the multi you could get a HELOC....

I find it amusing that Michigan City comes up in so many threads discussing good rental markets for multi family and rentals.

Please click on the links, give them a read, and share your thoughts in the comments.First is a post that I feel will help not get overwhelmed with the amount of info that is here on BP:https://www.biggerpockets.com/blogs/5868/52761-the-simple-guide-to-getting-started-on-bp The second is a post that will help get you focused with your real estate investing goals:https://www.biggerpockets.com/blogs/5868/52743-im-new-to-bp-any-advice-would-be-appriciatedThe last one is a post that will help you choose an “investor friendly” real estate agent.

Historically, I've had a lot of success with multi-families. 

The government does not control your business unless you let them by choosing to rent to S8. 

I always choose to "touch up".

I'm interested in small multi-family properties in which I could house hack for a year or two. 

Would someone be able to explain to me FHA requirements on Multi Units?

Keep things the way they are now and with all new tenants.Send out the proper notices allowing yourself sufficient time to replace tenants that for what ever reason choose to move.