I know a lender that can help with both states that does investment lending for very cheap, it would be worth a connection as you look to build out your team no matter what you decide.

You can start by not calling us Boomers, lol.

No pods. 3 rolls of paper towels.

I would generally say no if you don't have a property unless you're looking for peace of mind knowing that you've set your financial life properly. 

Yes, you need a team, however you can't just assemble people together and call it a team. 

Call it nicely it’s market inefficiency but recognize that Chicago historically is a very segregated city.  

Wholesalers (no offense to those in the comments) who are doing this without being a foreign entity are probably co-wholesaling which is on the borderline and practically acting as an agent without a license or getting referral fees by having actual wholesalers on the ground doing deals and they just provide the leads which is different than wholesaling.

No notable issues to date - mostly minor stuff. 

So, now rather than it being a "legal" issue, you just call the police, they are forcefully thrown out. 

With your organizational skills and people skills, you will put together a team in no time.