Throw me your thoughts for Hanover North for Two Weeks

[Gambit McCrae]

Needing to start compiling info for 2019's 2 week trip starting out in Hanover, NH(Dartmouth College).
Here's pretty much all I got so far, correct me if I'm wrong.

When: August 30th thru September 15th

Where: Hanover, NH NoBo ..... Grafton Notch, ME??? That would be 175 miles

Who: Myself and a hiking buddy. Both in better than average but not peak physical condition.

How:
To Trail: Fly into Boston, and take the Dartmouth Bus to Lebanon, NH. Uber from Leb to Hanover
To home: Grafton to Portland: Unknown but can get a shuttle if need be. Fly out of Portland, ME back to Nashville, TN.

My unknowns:
Is my time of year spot on? Accommodations/ sleeping locations in the whites. Curious about my daily mileage...Surely 11 MPD is manageable compared to my average MPD thus far on the trail. I do understand to expect less miles per day which is why I have decreased my MPD from 20 to 11.5