My wife and I have disliked how CA has been managed for many years, we're hoping to start a brighter future for our children.

I know there are many discussions on servicing companies on what we like and dislike.

I actually grew to dislike people who were nice or polite to me. 

My recommendation is that you contact all that have looked although have not pursued, ask them 1 quality they liked and 1 quality they dislike.

Even though I dislike small multi because it often attracts renters who think it’s like a home and suddenly discover how loud their neighbors are.

My wife and I made the "sacrifice" to live in north Avondale/Irving Park for a year and I very strongly dislike the neighborhood since I have no plans for kids and love city life. 

Its a huge reason why many people dislike / distrust the agents and the sales industry in general in my opinion.Other than what you've mentioned, if you are experienced and savy enough to handle a real estate transaction, then perhaps you don't need an agent. 

When you are a landlord the last thing you want to do is have your tenants dislike you.

@Joe ManriquezPersonally, I dislike when my clients get materials.

If you think you will work less, or have less balls to juggle by being self employed, you may be mistaken.Your lifestyle may improve (or may degrade) depending on how you how much you like or dislike doing the self employed things you must do.You might make more (bonuses) working W2 at 70+ hours than you will investing (in some positions, for some employers), others exploit their workers terribly, and treat them bad.