1. great tip line for parking issues - https://twitter.com/StoweMtAlerts?s=20&t=CRdOgQIFyeE1Ed_flca0cA
2. I think monday - friday you should be overall ok...parking is free on mansfield side and it's a huge lot, but on a powder day it could definitely fill up quickly even on a weekday
3. on that note if it's going to be a powder day you either want to get up there for 8am or wait til later...people have been stuck on mountain road well over an hour crawling up towards the base (even on weekdays)
4. last piece of advice on the commute - if you dont have 4 wheel drive or snow tires there is a very steep but short climb going to the mountain by the matterhorn, so if its snowing caveat emptor and all that
5. skiing wise youve got mansfield (the main mountain) and spruce. mansfield has the bulk of their challenging runs and some good cruisers off the quad...and then a few great cruisers on the gondola. spruce has lots of beginner terrain but also some good cruisers at the top off sensation quad (also - this lift is typically pretty empty so if the quad and gondola get packed this can be a haven). easiest way to get to spruce is to park at mansfield and take the over easy gondola across.
6. restaurant wise off the mountain you should be in pretty good shape on the weeknights - best casual spots are piecasso for pizza, the bench or the backyard for solid pub type food, and then rimrocks is similar but a step down (and super kid friendly). matterhorn is probably the go to apres ski bar (or the whistlepig spot at spruce base if you want to stay on the mountain). for better dining probably look into harrisons or plate on main street...and there is also cork a wine/tappas type place. and finally hen of the wood in downtown waterbury, one of the best restaurants in new england (not an exaggeration).
any other questions holler, but I appreciate you giving the opportunity to procrastinate work!