@Jonathan Klemm thanks for the mention@Ali Farhat Jonathan is correct that you may still have some opportunity depending on the Zoning designation for the lot, and how many existing units are Legally Recognized by the City.You can Check the Zoning Designation here on the Chicago Zoning MapFrom there, you need to check the requirements for your lot based on the Chicago Zoning Ordinance (Note: RS-3 does not mean 3 Units.

Mailers as a mono-action to lead creation is ridiculous, and this form of marketing has never been designed for such any more than a billboard is for getting "leads". 

The reality that neither view is realistic or probable.The best advice I can give would be to underwrite for long-term leases as that can be an acceptable exit strategy, but be prepared to execute well on your MTR strategy (great interior design along with profesisonal photos and concierge servive). 

if a brand new investor is working with a private money lender, it's almost like one party is taking advantage of the other (not saying it's intentional)

We have a few brand new construction projects in Florida.

For multifamily investments, using the LLC name is typically sufficient for legal and banking purposes, as advised by your CPA and banker.A DBA may be useful if you want a separate brand or manage multiple properties under different names, but it’s not required for most investors.

Her undergrad is in design with a heavy dose of building codes, etc.

BiggerPockets is full of resources designed to help you along your journey, whether you are just getting started or a seasoned investor.

We could sell that house by itself, but it would be sold under a land in common agreement and an HOA would need to be formed.I also confirmed with the Public Works department that a 2nd driveway can go in, with a septic designer that there's room for second septic tank, and with the public water company that they can tap into the main water line from one of the neighboring roads.I'm sure there are some more details that I would need to iron out that the code officer didn't bring up, but the high level answer I was looking for is that my town does allow selling off a second house under the LD 2003 legislation.

If you plan on building a brand or having more rentals, than 100% but if only planning this one it isn't fully necessary.