.✅ Stronger Tenant Relationships – Being involved directly allows you to build rapport with your tenants, which can lead to better communication and longer leases.Cons of Self-Managing❌ Time-Consuming – Dealing with maintenance requests, late-night emergencies, and tenant disputes can quickly become a second job.❌ Legal Risks – Chicago has strict landlord-tenant laws.

The squeaky wheel wins in development so I'd recommend you staying on all communication with the city so that you can see the communication and push as the owner.

On the other side, the bigger companies have more experience and their numbers tend to be more accurate (not always)... as they are big companies "their costumer service" and communication is better but at the same time they "have more mouths to feed" if we need to be honest so can get a bunch of ok or good deals but I kinda doubt they will be great (just my personal candid opinion).

Their price structure is probably different but I would use any free consultation available with all law firms that are specialized in asset protection before deciding what structure to use.Also this firm and one it’s lawyer (Clint Coons) have great YouTube channels that will give you a plenty of free information to educate yourself about some of the structure that you may consider.

This requires vetting their claims by reviewing EDGAR filings, property records, court records, Secretary of State filings and communicating with those who know more like city government, a more experienced investor, etc.

Be prepared to follow up multiple times, using different forms of communication—calls, emails, and if possible, in-person visits to their office.

Effort is still required to communicate with the Craigslist advertisers, but having software to lift the deals out of Craigslist would surely be worth $1,000. 

Keep things above board and hire people who have good accounting and communication.

It's a more involved discussion that requires one on one communication and no, joining a "community" does not prepare you.

At this stage of your life, communication skills are most important so be sure to develop those.