I will definitely be looking for local investor meetup events around the Chicago and greater Chicago area.

I highly recommend attending real estate networking events to meet more people is this space and pick their brain and learn more from their projects and see what is working and what is not.

Has anyone tried to operate a business on a plot of land with minimal development until it builds revenue for a structure (flea-market, private park, outdoor event venue, etc)?

Since you’re leaning toward multifamily, it might be worth connecting with local investors or brokers to see if a license is necessary for your goals.

I started my OOS HML  career in Detroit and that was 2002 and WOW coming from our area what an education I got.. my clients that were doing turnkey at the time and all the buyers were out of state ( basically LA based) the local on the ground operator was very good he had all sorts of tricks to try to keep the houses safe.. the one i really liked was painting the copper pipes grey so thieves would not steal them..

Phil Alexander, the main guy, does not hold the local providers accountable.

For example Airbnb collects and remits all state and local taxes in Pinellas County but only does 1 of the 2 in Bradenton county just south. 

I am checking out their 3 day event starting Feb 29th.

I'd recommend the spread on the return and your ability to replace damaged items (local vs. not local, strength of your team) be the determining factors in that decision.

If that's not possible, find a local investor and work on sourcing the deals to partner up.