I used to live in northern Illinois, so close to Wisconsin - there are several smaller towns around lakes that would be good for short term rentals. 

He gave me short notice.

With many people's help I recently made my first buy-and-hold purchase of a duplex in Fort Wayne, as an OOS investor! 

Even short comments from professionals seem like much better alternatives than my deep contemplation.

If you are short on Capital, but heavy on sweat equity you want to play to your strengths, so using the banks Capital while you force appreciate a property you live in is a good way to build equity.  

I am also probably not buying anymore in the near term because I can get similar returns from the tech monopolies without the work.

If I were to do so, I'd definitely look for small multi-family as opposed to SFRs, unless you're wanting to create a short-term rental(STR). 

I thought about starting out with 1 single family residence for long term or midterm rental.

I would try to find a short term/mid term rental friendly agent who might be able to give you super accurate feedback on the market

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