I'd say you need to realize than working at Fedex Corporate (or somewhere similar) is a career goal for 95% of corporate pilots---just like being a Fedex 777 Captain is a career goal for 95% of airline pilots.
Fedex corporate takes a a few thousand hours, probably some PIC time, probably a bizjet type rating, and probably a recommendation from 1 of their 50 (?) pilots. Cargo side takes a few thousand, PIC time, and a few recommendations (which you can get in about 10 minutes with your dad's connections and a little time at a regional airline/military base).
Corporate probably does not care about your dad's 30 years of service or his MD11 experience.
If you're going to be in the military guard, corporate jobs and even charter jobs will be trickier than you'd think.
Like GalaxyFlyer said, there is a back door from the corporate to cargo side, but not many have went through it (corporates pretty good in other words). There's a similar backdoor between the Fedex sim instructors and the cargo side.
I'd focus on getting to the left seat of a jet so and once at 1000 PIC, you can fill out the cargo app.