I am looking at 2 buildings right now with elevators and current landlord has maintenance contracts in place covering the elevators for a set amount per year and then what I'm assuming would be discounts on service and parts above and beyond routine maintenance. 

Any advice I can provide is strictly from my little experience and the education I’ve gotten in the last two years.

If your bookkeeping/accounting  system allows subcategories, then add subcategories to the "carrying costs" category for each specific element of expense such as mortgage interest, hazard insurance premium, property taxes, utilities (water, electric), yard service, and other routine maintenance and upkeep items.  

I don't think they are as strict about having all of the money right away like a trustee sale would be but I am not 100% sure.  

The Town of Vienna has strict regulations and I caution you to do your research and really understand local codes before diving into that market especially.

You had best be very strict with your expectations and time lines for him to shape up.

How many of his students actually routinely close deals?

I am working as hard as I can though to get back home to get personally involved with the day to day routines with my company. 

Rich Dad Poor Dad is great for adopting the investors type mind set but is not strictly a real estate investing book. 

In terms of getting the license, note that PA has fairly strict regulations on what a salesperson can do.