Where has everyone had luck in the midwest investing in single/multi families and generating cash flow/appreciation?
To succeed in Midwest investing, IMO, you really need to know the local markets. There are lot of retail stores going out of business and some pockets in the Midwest states are declining in population (smaller families). But there are places like Madison, WI that are growing and there is money to be made with student housing (rental homes) and apartments from young professionals getting their first or second jobs out of college. Income isn't that great though for a city of that size. You would get a lot of healthcare, Epic, university, and finance workers.
Hudson and River Falls are growing. Northern WI is really struggling but there can be good deals to be made, but you have to know the risks to best get around those risks.