Your question is a bit confusing, but here some answers  : We always need a passenger in the shutle, in boyh way. since Terry is at the limit capacity, he is always alone on the shutle, whitch mean that we need someone in the station to get the last pilot after Terry, since Terry can't be the last one. Here how you can do it  :

I can't prove that it is the best solution, but it easy to prove that 4 can't be a solution, since the answer need to be odd.

Your question is a bit confusing, but here some answers:

We always need a passenger in the shuttle, going both ways. Since Terry is at the limit capacity, he is always alone on the shuttle, which mean that we need someone in the station to get the last pilot after Terry, since Terry can't be the last one.

Here how you can do it:

I can't prove that it is the best solution, but it easy to prove that 4 can't be a solution, since the answer need to be odd.