Thanks for laying out the important stuff so neatly.

Quote from @Kar Sun: My tenant's lease is coming to a close and I am relieved she will be moving soon.She has been paying on time but has been extremely unpleasant and rude.While the money does not smell my mental sanity is more important than money in this case.She sent me a registered letter stating that she feels "unsafe because we have not done the fixes the way she wanted it".She requests to have her witness for a walkthrough.In my state a walkthrough is required but I am not about to grant it to her to bring any witnesses as that is not in my contract.If she feels unsafe she does not have t be present.I also do not treat a final walkthrough with a tenant as a final sign off.This walkthrough does not include a detailed inspection of the plumbing and the appliances that will be done after she departs.This is simply for the visible cosmetic issues and should take less than 1 hr.  

That might be the single most important point - 2 out of the 3 properties have come as off market deals through our network, and we also found our attorney, accountant, agent, contractors, etc through our network.

One of the most important skills you didn't mention is networking, which you are obviously doing well at too.I'd recommend connecting 1:1 (zoom, coffee. lunch, etc.) with a couple from the BP Chicago community or better yet check out some of the local meetups: https://www.biggerpockets.com/forums/521-real-estate-events-...Make friends with the meetup hosts...they will often know whos who and can help you make the right connections.Regarding your license, I think it's a great idea if you have the time and are going at it with the right intentions. 

@Hal RobertsThe biggest challenge is obtaining accurate and current data, such as demographics, job growth, and most importantly, rental data.

Verifying last 2 years of rental history very important!

There is nothing more important than investing in family. 

A process is far more important. 

By offering strategic guidance, the broker helps investors make informed choices, ultimately increasing the likelihood of project success.Finally, a good private money broker understands the importance of post-funding support.

It is fairly important but out of your hands how the neighbors receive you but especially self managing you will want 1 or 2 neighbors on your side.