@Josiah Hrusch...lots of mixed advice here, but I don't see any qualifying questions...you tenants are unlikely to have 100% voucher coverage...so, there is probably a private pay element here as well?

The statute also states that each affordableaccessory dwelling unit shall apply toward satisfying theaffordable housing component of the housing element inthe local government’s comprehensive plan.

@Justin G. mentioned the most common economic structure, but there's no right way, and that's just one element to a structure. 

TIP:  If you a negotiating an insurance settlement and the Insurance Adjuster refuses to pay for electrical, HVAC or re-piping due to a fire, you may wish to hire a Professional Engineer(s) to inspect the property and render an opinion as to whether the electrical, HVAC or plumbing need to be replaced.Thursday - Meeting with GC to discuss start of renovation work and status of bids received by GC for various elements of the work.

While statutes vary widely between states, the basic element here is that you, as a payor, are considered a “volunteer” meaning, you paid a decedent’s secured debt without having any apparent claim or legal standing. 

Making an all-cash offer simply means making an offer using cash in a transaction that carries no element of risk in it from a bank that might choose not to lend.

Outside of looking at structural elements of a house, it seems that there may not be too many issues to consider? 

How would you indemnify them when they are the one marketing, screening, and interacting with the renter?

Specifically in Chicago, any advice on which types of rehab elements an investor in multi-family properties should focus on or give more weight to when deciding how to rehab a multi-family property? 

General Contractors- Network, network, network..... but you should not bother with General contractors until you have everything in place to run a business.So I just answered your specific questions but flipping homes is running a business & it takes more than the elements above.