What is the best way to file and fly to an airport that has only 1 or 2 approaches using a transition? Normally how I teach my students is look for a fix or VOR on the enroute chart that is on as many approaches at the airport as possible. That way you could navigate yourself onto the approach with out ATC interaction (in a radio com loss situation). Generally, I get my approach instructions from ATC prior to that fix.

Let's say you look at an airport and it has 2 approaches, each with a VOR that can be used to transition from the enroute to the approach. I file my airways to that VOR. For instance, KBAT D-> ABC V555 XYZ and the destination is KHIJ, where XYZ is the VOR that can be used to transition onto the approaches. However, upon reaching the XYZ VOR you have received no ATC instructions. Do you proceed along the route to the initial approach fix for which ever approach is most suitable? Would they expect you to do that? This is assuming normal radio communication and you were "cleared to the HIJ airport as filed"

The situation that happened with me was similar: we reached the XYZ VOR but we were with another approach. IE we would have to be handed off to someone else before we got an approach clearance.