By the time I retire, I want to have enough rental properties to have financial independence to enjoy my hobbies and enjoy spending time with my family and watch my children grow up.

Setting financial and lifestyle goals and using lessons from your current setup can help.Good luck!

I am financially free with ~$10-17k/mo cashflow.

I would like a payoff planner that helps me navigate the various maturity dates and interest rates of my (15 due in 5) mortgages so that I gain the best financial advantage when paying down principal balances. 

FHA gets a bad rap because sellers and many agents think it's only for people who don't have the money so if I had 20 percent, but wanted to use FHA, I would present a proof of funds with my offer showing I have more money, but am using the FHA as a financial option so I can get an investment property as well somewhere else.

Are you wondering more about the financials of it or operations? 

I would think in most situations the original owner is in financial trouble, probably delinquent on their mortgage and facing foreclosure.

My wealth was tied up in assets and I wasn’t at a place financially to not work.

The financial analysis side of CRE really excites me.

Ideally your alter ego can do it, but for some people it is better to ask someone who does not care one way or another.