I'm actually a CFI/II myself, but don't have a lot of experience picking up clearances on the phone/GCO out in the boonies. My peers are in a similar boat.
I'm not actually planning on doing something like this anytime soon (no need to worry cubdriver!), I'm just looking for the "proper" method as to go about something like this....so if possible looking for people who have flown out of airports like this quite a bit back in the day (prior to GPS being commonplace).
As for example airports; 8V7, OZA, JHN.... Basically airports on an enroute chart that are in the middle of a sea of white, or just next to a Victor airway, but no VOR anywhere relatively close. My question mainly spurs from the fact that if you aren't equipped for RNAV, you can't navigate directly to an intersection....your only chance would be a vector from center, and in the case of lost comms on departure, the departure clearance would have to have some vector, "...upon entering controlled airspace turn right heading tree-six-zero to intercept Victor sixty-six..." But is this how it's been done? Whatever the method, this would have been very common prior to the mid 90s.
As for arriving at airports like this, that's no problem. Just pick an approach at the airport, find the IAF or enroute/feeder fix on the approach plate then find it on the enroute chart....it's the departure that I'm confused about. Speaking of which, whenever you call FSS or ATC on the phone or RCO or GCO, they always want to know what runway you're departing in addition to how long until you're ready. I'm guessing this has to do with it also.