You should connect with @Fed Finjap; I just saw on another post that he is also buying in the Chicago neighborhood ofLakeview and he recently went through some lessons learned on a 3 flat in Chicago.Check out his post:  https://www.biggerpockets.com/forums/922/topics/1223655-refl...

Milwaukee inventory has just been so low, that even very distressed properties sell to first-time home buyers without a significant discount, so in the end it's cheaper for me to buy properties that already have a new roof, windows, kitchen, HVAC etc

Both bathrooms need a complete remodel as well as the kitchen, the ceiling in 2 of the bed rooms are bowed (previous roof leak that was fixed) so new ceiling drywall, appliances, flooring, and paint throughout.

If you buy a house you get a full inspection and check all its points, termites, roof, etc.

Sometimes you can find a large enough company that you can sub everything out to them and get paid on a commission or flat fee basis, or you can get the property platted and sell it that way.

I think the A frame idea works great for this setting, but some have said the A frame style steeper peaked roof works better. https://www.instagram.com/redtail_cabins_adu/

It's an A-framed garage with shingles roof, gutters, windows, and a 32" exterior door (in addition to a 16' operating face door). 

It's a 4 bedroom SFH for $325k, built in 1990 and it's got many upgrades including a 2024 roof.

2 unit house 30 year FHA 6.6% major renovations (roof,bathrooms,kitchen,etc) home has appreciated 397k when appraised to 550k zestimate (similar comps in the area are 500k).

Then roof starts falling.