Payroll, bookkeeping, etc can mostly be done remotely.Here is a great list of questions to ask a potential accountant:http://www.biggerpockets.com/forums/51/topics/70447-questions-to-ask-a-cpaAlso check out the www.NAEA.org page in your search.

I am doing more video calls, I’m revamping my book keeping, I've dedicated a separate room as a home office and basically spending more time properly running this business the way I should’ve years ago.  

Being a great contractor usually makes you a lousy bookkeeper. 

I realize it's more bookkeeping, but in the long run at 400 properties seems like the odds would have been in their favor to liquidate one entity, with that financiers permission than to hand over all potential earnings.

Regardless if you are solely an investor or do decide to become an agent you are essentially running a business which requires book keeping, expense tracking, marketing and countless other tasks that I am certain a degree could help to build the framework for. 

Have you considered outsourcing your accounting to someone who is well rounded in real estate accounting as a financial analysis and an accountant/bookkeeper/cfo/controller?

It may seem like a large and largely unnecessary expense to hire a bookkeeper to set up your software and your accounting systems, but it is absolutely necessary.

Im a bookkeeper so not starting from scratch but I don't know nearly enough about real estate taxes and optimization to do it myself right now.

Maybe she is the negotiator that makes all the calls and does the book keeping while you do the repairs. 

My wife does the bookkeeping and pays bills (switching utilities and does the paperwork with moving people into properties.)