What are some legal aspects of investing in Milwaukee that are the most challenging for investors?

A realtor uses a standard legal contract that licensed agents are required to use in Utah. 

I currently made an offer on a legal “duplex” that is 3/2, 3/2.

Others are more savvy with that stuff than me. https://www.nolo.com/legal-encyclopedia/overview-landlord-tenant-laws-illinois.htmlhttp://www.ilga.gov/legislation/ilcs/ilcs3.asp?

In Dodd Frank, they anticipated that some might carry paper to get around Dodd Frank (not that you are doing this) and therefore they also "cast their net" over seller carry backs.Most importantly, please don't rely on what I say, except to inspire you to seek legal advice (which I am not qualified to give) from a qualified attorney in this area, and structure this so it doesn't get you into legal tangles or possibly worse, interaction with the CFPB.

The usury laws from what I have been able to learn about in California are very ambiguous as to what is legal and what is not. 

The last company I interviewed though takes a holistic approach and looks at tax efficiency, insurance, POA, will, and have in house legal and accounting.

First thing I would do is check the zoning to see if it is legal to create a separate apartment in that space.If zoning allows R2, then it could work.

in Oregon U cannot.. in CA I suspect if someone filed a complaint you would have an issue.I mean other wise why even have real estate licenses.. anyone can just do anything they want like China.deals do get assigned all the time but as you state usually without any advertising. 

The legal limit for interest on a mortgage is 20%; therefore hard money lenders are well within their right to charge 10-15% in exchange for the risk they take and the benefits they provide.