I personally think being a landlord in Chicago is easy and I have never had an eviction. 

Caution:  Personal credit card financing is a huge risk and good luck finding 0 percent interest today.

Personally CA scares me. 

I’m not convinced it makes a real difference unless a person has a unique setting.

I personally have no connections with anyone who is involved in this niche and I'm wondering how other people have started their journey.

By year 5 we had around 55 people.We did hire a marketing person but frankly marketing wasn't our strong suit. 

You’re still going to be personally sued when something goes wrong. 

Try being an agent, your phone number is EVERYWHERE and you get targeted by a whole industry that wants to sell you the latest gimmick.Here is what helped me.I answer calls and when it's a telemarketer I will interrupt them and say very friendly (because I don't hate the poor person who gets paid to do this and coached to be ruthless): Hey, so glad you called, can you do me a big favor? 

When your LLC takes a loan, expect as members to personally guarantee the debt.

You look like the kind of person who is going somewhere.