I think your idea of staying somewhere more centrally located than Manchester is a good one. If we didn't love where we stay and love the owners (who actually live next door and are often there when we rent), and also feel like it's our place since we've been going there for so long, we would probably stay somewhere that was more convenient for getting to other VT locations. Someday I would really like to travel to the NE Kingdom.
We usually visit Quechee (must do Simon Pearce glass), Norwich, Manchester, Weston, Woodstock over a week, so as I said before, from Jamaica/Stratton, it's a lot of driving time. We went as far as B&J's in Waterbury last trip and combined it with a side trip to an amazing cemetary in Barre.