That is indeed one of the strategies I plan to implement. 

How do you go about tracking information about your properties like what size air filters or other specs you might need to reference when out getting parts for a unit, when preventative maintenance tasks are due, what keys are associated with it, data on major equipment, etc? 

The normal groups are hard to hold right now, but they should be implementing Coffee in the Park here shortly.

Conversely, any strategy we consult on and decide to implement is quickly and efficiently handled if we prepare the returns. 

A nearby military base keeps the area stable and recession resistant, but it also prevents any real job or production growth here.

With your situation above I would focus on what was not disclosed in the condition report/seller discloser report (if you got one or even have one in your state) and'/or focus on the item that the next buyer might want to be fixed as well and/or things that will prevent you from getting financing.

This method will eventually be implemented there as well.

I am likely going to pay it, but any recommendations on how to prevent it in the future would be great!

@Michael Clay  Personally I've found that regardless of wanting to do this (getting OF and then re-selling with OF), the sellers attorney will put in language to prevent it. 

What background history can prevent you from obtaining your license?