For example, you could get your plot zoned and subdivided and then sell it to a homebuilder.

Hello,  I purchased a legal 3 flat in Chicago (RS-3 currently zoned) that that we are gut rehabbing and are looking to convert the basement into a 4th unit. 

I own a property that is in an AE zone flood plain.

Who should I contact to help draw out potential layouts of use for the land that would fit the zoning?

I looked up the property, and it's zoned for high-density residential, and it's three blocks away from a regional university (I live in a small college town).

@Elaine Lee Make sure your property is zoned for this use, or that the bylaw reflects this being allowed.

If it is two different buildings, you’d have to go your planning and zoning dept to see if the Parcel could be subdivided.

I don't see anything in your post that would be a red flag for commercial.There are certain fees you cannot get a multiple discount on... for example, you will have to get an appraisal for each property, title fees will be per property, pre-paids (taxes and insurance), etc... you can't get any big discounts on these.. they are what they are. 

The zoning enforcement officer shall require that a declaration of the accessory family dwelling unit for the family member, or members, and its restrictions be recorded in the land evidence records and filed with the zoning enforcement officer and the building official.

These cities tends to command quality tenants and they have great schools.In regards to the FHA loan, The FHA 3.5% is very difficult to get accepted contract in this highly competitive Red HOT Real Estate Market across the major metros in the country.I will suggest you get a 5% Conventional Financing.