Complex Filings: Businesses with more complex structures may choose to prepare and wait for further developments.What’s at Stake?

He flipped houses, built apartment complexes etc....so that's where me wanting to do all of this comes from.

Plus, very important to understand the new layout and how the dig down will effect the existing stairs, plumbing, etc.Happy to connect and talk through your specific situation because @Bruce Woodruff mentioned every project is different and know one price fits all espeically with these complex jobs.Where at in Chicago is your building?

From SFH BRRRR, flip, or complex syndication apartment deal they all require effort.

My apartments are in a lower income area, so I don't want it priced too high where it is going to scare them away from applying.

Quote from @Andrew Self: Previous apartment.

Fair enough, I have partial ownership of a commercial (apartment) building in the Bay Area and I would estimate it as a Class A- to maybe Class B - great location, great tenants, nice amenities (not high end like gym, new pool, community room with big screen TVs, etc), high rents, but building is older (built in 1950s).One investor I saw post that they look at where Starbucks and Costcos are opening and possibly factor that into looking at different markets.

Because of cost, duplexes are are a better choice and compete well with SFH and or apartments. 4.  

Your situation is a little more complex than most people and I highly suggest you consult an attorney. 

Your best route might be to buy a 2 to 4 unit property that you can live in and rent out the additional apartments.