Mooneman,
You’ve got lots of flexibility as far as transportation and you should be able to get up into New England a bit in 3-4 weeks. There is bus service from Great Barrington and North Adams/Williamstown and Pittsfield MA, all easy to get to from the trail. Also Bennington, Manchester Ctr and Rutland VT has bus service and if you get kinda adventurous and move quicker, so does Hanover NH. Please check these stops before you decide on a plan as I know Greyhound has been drastically cutting routes lately as they’re not doing well. The point is, you’ve got tons of flexibility and shouldn’t need to pick an ending point and the start of your hike.
This section has quite a few deli's and restraunt stops, particualarly in NY. This is nice because you won't always have to carry much food, more than a couple days worth and many of these stops are really close to the trail (a mile or less).
Definately try to spend a night at the secret hostel which you'll most likely hear about once on the AT. Worthington's Bakery unfortunately closed. The sunrise pavilion south of mashipacong shelter is great for lunch or sunsets but no camping.
As mentioned Graymoor Monestary in NY is a must stay as well. RPH is a nice shelter that most folks enjoy.
I highly recommend Ten Mile river campsite and shelter. One of my favorite spots to camp on the trail. The Mounntainside Cafe near Falls Village CT is a great spot to have a meal, right on the trail. Rands View is incredible, so spend some time there! The whole section of trail between Salisbury CT and JuG End rd in Mass is pretty great and there are tons of good camping options (Riga shelter, Sages Ravine, Race Mtn, Hemlocks Shelter etc.)
Upper Goose Pond in Mass near Lee is a must stop. The cabin is great, you can canoe and the caretaker makes AYCE pancakes for 3 bucks! You can't beat it. Dalton Mass is a great little trailtown and you can't go wrong staying with either Tom Levardi or Rob at the Bird cage. Both places are esentially free.
If you get up as far as Vermont, Glastenbury Mtn, Goddard Shelter, Stratton Pond and Mtn, Bromley Mtn, Spruce Peak Cabin, Cooper Lodge/Killington, Little Rock Pond, Big Branch shelter and Baker peak are all cool places to camp or check out sunsets.
Most likely as mentioned above, thrus will be racing by you complaining about being bored while you scratch ur head. Yes this section is not as fantastic as the Mahoosucs or the Grayson highlands or smokies, but there are some real cool spots and you can get there with a good deal less effort. Take ur time and enjoy. And yes southern NY/Harriman park is a lot more difficult and frustrating than the profile maps lead you to believe so take ur time and don't expect too much. Enjoy!
A-Train