So you reach out to your parents, your grand parents, your aunts and uncles, all your friends parents. 

I am not sure how well this will fly at some of our Chicago properties in Grand Crossing haha

Just know a headache will eventually come, but a plane ticket isn't that much in the grand scheme of things...

I cover the I-94 corridor out to the Lake, and the 131 corridor to Grand Rapids.

You might try to look in Grand Marais, there are a few lots listed on Zillow currently.

Personally college took up way to much of my time during my startup construction company when I could have been hiring more people and making a few hundred grand more.

She couldn’t do a self directed account because grand kids would be disqualified. 

I also have properties in Kalamazoo and Grand Rapids.

Seems to be a lot of inventory of cheap 2-3 families that require some work but would cash flow, and you're only ~40 minutes from Grand Central on the Metro North New Haven or Harlem lines.

If I did not live in Michigan, I would be looking to invest in Michigan.You can easily buy several cash flowing properties in a place like Lansing (the State capital) with that budget or one class A property in a location like Ann Arbor, Grand Rapids, or Traverse City.Also, while many areas are seeing rent increases slow nationally, Michigan is continuing to see solid demand for rental housing.Michigan has a temperate climate, abundant natural resources (especially water), and a diverse economy.To your success!