Your local REIA group should have a list of proficient Lawyers for you to interview.If your not affiliated with a local REIA use the link below to find a local Real Estate Investment group. 

I know I want them to be proficient in Buildium, or at least trainable.

Should be proficient in creating reports, excel, etc.Perfect for an eager, go-getter who wants to learn the business and gain experience.Send a message if you are interested in this role.

Question #4 is the one most in my wheel house, so I will start there.The first step on this or any investment property mortgage question is to make sure that you are using a lender with proficiency in investment property finance and the ability to originate mortgages without overlays.You mentioned "broker", and although your mortgage person may be best in class, you truly need an originator that can go straight off Fannie/Freddie guidelines. 

Either become proficient at determining these yourself or team up with a trustworthy agent and/or G.C. experienced in determining true market values and rehab estimates.

You seem to be more concerned about funding before you are really proficient in negotiating a great discounted property.Money for real estate will come once you create the great deal.

I "left" high school at 16 by taking a proficiency exam (comparable to a diploma; not a GED) which was available in my state.

You are right business is risk, so I want to start slow and get proficient at it.

Look, there is all kinds of owners right, I have seen some who do leases a step above bar-napkin, so really one can find all kinds of actions int he segment but for argument sake, let's talk about the "standard" which is utilized by the most professional/proficient in the segment. 

I have experience in project management and proficient in administrative duties.