Most markets will have just a couple of brokers who control most of the deal flow.

I manage over 100 doors that we own now here in the Chicago suburbs and I think it is mission critical that someone from management be there to oversee and do quality control on certain types of repairs.

.- I get 100% control over operational decisaions.   

These type of things you can't control.  

Your advise of backwards planning or reverse engineering is an excellent approach that becomes even more effective when identifying risks and mitigating those with various controls.

Locally There’s 25 rent controlled units that are 5 months old that you have to make between $37,000-$75,000 to live in and probably 120 units that are between 10-20 years old.

Any great self-managed property needs a high-quality photographer, handyman, cleaning crew, along with other property vendors as necessary (pool care, lawn care, pest control, etc.)What tools can I use to automate tasks?

Any great self-managed property needs a high-quality photographer, handyman, cleaning crew, along with other property vendors as necessary (pool care, lawn care, pest control, etc.)What tools can I use to automate tasks?

Like anything else in finance, if you have no self-control this is not a good strategy. 

Hey Kweli,My best piece of advice is for you to follow a path in real estate that suits your talents/qualities:Wholesaling - Sales & MarketingAgent - Incredible people skills / networkingFix and flipper - Great eye for design, construction, budgeting Buy and Hold - Patient, budgeting, you currently enjoy what you do for a livingETC.Overtime many then venture into different categories (I know I have)  but I would suggest you start with the one that suits you most.