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I think St Johnsbury, VT at the intersection of 91 and 93 would be better than Littleton, especially after Lincoln goes in. It fills the 91 gap well between West Lebanon and Quebec, while still being useful for White Mountains travel.
Agreed on Portland. It's midway between me and Bar Harbor (and would reduce 2 stops to 1).
You mean Conway? Not many people are going through Conway going to/from ME. The easiest route is usually to head south to 101 (Manchester to Portsmouth). From northern NY? It's probably best to head down to Albany and across on the Mass Pike. Both longer mileage, but usually quicker.
Going east/west in northern NE is almost as much fun as DIY dental work.