The cache will not be too hard to find when the ground is clear. Once the snow packs in, you will have to dig in some rather uneven terrain. It is not much below the 2K contour, so at least you'll get some views during your search.
The terrain rating is for winter access. Yes, there is a road to the top, but it has downhill ski trails crossing it in snow season. If you hike/ski/snowshoe up the back side from 42 28.482 / 71 53.026, you can hunt the High Meadow cache along the way. Taking the ski lift to the top will drop you quite close to the cache. If you try taking the Pine Hill trail because it is "shorter", the terrain rating goes UP, UP, UP.
The logbook has a number of entries already. Some are from cachers that "attended" my 2000th find, and a group that continued on to the summit made a test run on the cache.