I'm also actually attracted to the slower, more stable economy of GB and Wisconsin. 

Think of what kind of tenant you want to attract.

The potential speed that I could send my money out and get it back by lending is attractive. 

One of the attractions for me of a single-family home is the extra space for storage, such as a 2-car garage or storage shed in the backyard.

There are quite a few pockets that offer this price range for property that attract renters and rents are up. 

The area is super-boosted by the destination wedding location, and the views and water access of some properties make it super attractive. 

And honestly that's what makes REI so attractive, taking a simple concept like house hacking, and turning it into a creative investment.Consider living with roommates(as many as you can), in order to lower your cost of living, and therefore increasing your potential to stack some cash.

If the community is stable or has a lot of rehabs it wont scare me away or attract me unless I see a good school, hospital, and/or large company within 10 miles of the property. 

Is the property in an area that will continue to attract tenants, or is it a miracle each time you find a tenant?

Desirability of the area for renters (access to major roadways, attractions, shopping, nice neighborhoods)2.