People do the whole AT with dogs all the time, so the 100 Mile Wilderness should be just fine.
Definitely make the side trip to Gulf Hagas. Most through hikers only go to Screw Auger Falls (0.2 off the AT), but the best of the Gulf is much further up. It's worth the side trip.
Cloud Pond Lean-to and the Antlers Tentsite are both incredibly beautiful places. Spend the night at Antlers for sure.
Also, there's a barely marked side trail just north of Rainbow Falls Lean-to that leads to the edge of Rainbow Lake, and a Nature Conservancy campsite with an amazing view of Katahdin. Another really amazing campsite.
That's as much as I can think of off the top of my head. There's not much on the AT that can compare with that stretch of trail.