So are there any specific pros/cons to home style vs choice renovation?

You will have to reseatch the specifics of your area but in most areas the longer stays need a lease vs. a short term rental agreement.

Any specific cities/areas you recommend?

If you have a specific questions I'd be happy to help.

There is an MTR facebook group, but not specific to Milwaukee. 

I have not used Evolve so I can't really address your specific question.

My husband and I were legally separated when I bought the home and had since reconciled and ended up with two houses.

Postcards can work, track your numbers, be specific with your data, have a process in place on how to convert these leads and you increase your chances. 

Happy to send you some Detroit specific resources if you'd like.

Goal (in order of priority): 1) Convert upstairs of detached storage unit in back into 3 bed/2bath (for the downstairs, keep as garage on one side and rec room on other side), 2) convert detached garage in front into 1 bed/1bath for our grandma, and 3) eventually add a prefab home on the lot.From our research so far, I believe we'll have to do an SB 9 lot split in order to legally build all structures (but we're not sure if we want to do this now, or just convert the back unit into an ADU first then do SB 9 later).