I would agree with @Bill Gulley that the finance portion of the business is readily available to study and develop using the skills you already possess.That said, I believe the way to develop proficiency in a trade is to apprentice.

My purpose is to make it so my business accommodates my real estate ventures, much like a professional mechanic may be more proficient at buying and selling cars than your average investor.

I need help figuring out how to get the wholesaling and assigning strategies up and running proficiently.

A service worker who's proficient in building construction and the living situation can be an asset.

If anything, you'll at least be proficient in writing offers when you get a buyer.  :-)

It is extremely difficult to get proficient in an area without having trustworthy "boots on the ground". 

I'm getting my license now, I start classes on tonight, so hopefully I'll learn these things a little more and be more proficient at it. 

Tactically and technically proficient at all the jobs so you can spot and smell BS.  

Check with an attorney proficient with landlord-tenant laws in your state / city and see if this is an option in your area.

This is a simple task that all owners should become proficient at performing.