I enjoy the process of turning something that is entirely run down into someone's dream home.

It wouldn't hurt to hold onto some properties for the long-run and treat them as rentals year-after-year.   

Go to the Premises, knock on the door/ring the doorbell and wait.a) If all adult occupants are home/available, place a copy into the palm of each adult occupant’s hands, and leave one additional copy forany other occupants, ORb) If a person of suitable age and discretion is home/available, place enough copies for every adult occupant in their hand AND mail to eachof the adult occupants, plus one more copy to “All Other Occupants”.

Find a good investor-friendly real estate agent, formulate a plan for the first one, see some homes, run some numbers and then buy. 

There are plenty of run down properties in Wisconsin, there is always demand for something that is nice.

Or if you wanted to run a real business, becoming a private lender would clean up, but it's a lot of work. 

My comments are related to how I run my appraisal business.

Did you run title?

There are several ways to run and make sure you are maximizing your rental income while keeping your living expense as low as possible.

(I don't know why I can't tag either of you... grr)  Until last week I lived in Los Angeles, and it was no trouble at all to run them from there while working my 16 hour/day day job.