We just go by the calendar. Of course if something big came up, we'd find an alternate harbor to stop. We've always figured that we could put up in Boston, say Cottage Park, and take the T back home. Just like, on a smaller scale, going for Portsmouth over IofS, based on the wind when headed down from Casco. All long days can be tiring; if there is a short one mixed in, you can feel a bit like you are cruising and not delivering!
When we've stopped at Great Misery, the run to IofS, through the Annisquam, has been pleasant and relaxing. Once we went from Casco Bay to Matinicus, which put us directly beneath Pen Bay. A lot to be said for the overnighters; you just have to want to do them. And they do still hold some attraction for me; it's just a matter of crew. But if the recovery days are too many, nothing was saved.
The staging idea came about more from fitting in other summer activities and where to meet up to start. We used to talk about staging from Boston but just too many transportation issues. Not like we're about to cross the pond!
Yes, now being retired (one of us, anyway) could change the plans. But then it's also a matter of our cruising partners and their schedules. There's always the option of leaving the boats in Rockland (say) and returning in a week or two for more.