There's also less risk in the property I'd live in because I'm confident I would always pay rent, lol.Once I have the second property inside an LLC, I'll convert the first property to a conventional loan, then put it in a separate LLC.

Having a bad resident that doesn't treat the property right is always a risk, but you should have some confidence that the house is renovated correctly, the right paint has been used and if the resident is a little rough on it, it won't fall apart.I would ask from some relief from the company you purchased from (at a minimum pay for the deck repair).  

I am overwhelmingly confident that had I moved, my professional career would have not progressed as fast or as well as it had here in the bay and I’d have likely encountered fewer wealth creation opportunities.

Keep doing that until you are confident that you know what you are doing.

How confident are you in that $20k renovation budget?

I'm not fully confident on the tenant laws in DuPage Co, but Cook Co and Chicago are very strict on how landlords handle deposits, making it very easy to accidentally open yourself up to lawsuits.

Maybe I would be more confident with more information and after reading more, but I don't want to be in a position where there is any uncertainty in what I am doing, while simultaneously not being responsible for all of the consequences.

You will begin to identify good deals and have confidence to accurately price an investment position that works for you.

This would allow us to see how close we are getting and eventually build up a person's confidence to pull the trigger on an offer. 

I managed constructuring for years before investing or becoming an agent, and can attest to how detailed you need to be until you know the person you hire well, so well that you feel confident they can read your mind.