Saugatuck, South Haven, Grand Haven etc offer close proximity to the Windy City.  

Basically, it is a way to buy access to Presque Isle, and Grand Lake (the large lake you mentioned.

I have a tenant who says he will move out on lease end date, but is 8 grand behind on rent and I don't trust him.

I like the suburbs of San Antonio, Austin, Madison, Milwaukee*, Grand Rapids**, Chicago (no need to hate on IL, here comes marijuana legalization to increase all sorts of RE profitability). 

Purchase smaller property other than SFR, finding one that may need some TLC (but not a complete fixer) and put a couple grand to renovate it while you live in it for a couple of years and then refi cash-out and then begin filling it with tenants and buy another spot.

One in Phoenix, 3 in Apache Junction, 1 in San Tan Valley, 1 in Florence, 3 in Coolidge, 1 in Casa Grande, 1 in Arizona City, and 1 in Eloy.

They like the home-run or grand-slam deals.

It's a few grand a year (at minimum) to maintain a license -- the usual advice is if you're not either 1. selling as a full time job, or 2. doing enough volume to justify holding a license, then it's probably best to just hire a great agent that does it all full-time -- you'll get better negotiation and a better knowledge base.  

In 10 years of being a landlord in SV, I have had a grand total of 2 weeks of vacancy.

Reach out if you want more details on Grand County.I live in Evergreen.