Valid points. You sound like someone who might enjoy the
Indy Pass. Believe at this point you'd have to sign up for a wait list and probably couldn't get it until next season, but no harm in getting on the wait list. It's cheaper than the big mega passes and includes some mtns in your region, as well as some around the US that you might aspire to visit including some pretty good ones in New England and the Rockies.
BTW, in 2003 I packed the family minivan with six of us and drove VA to CO for my kids first ski vacation in the Rockies. All that time on the road with a van-full was brutal, but we saved a bunch on airfare and enjoyed skiing Loveland, Winter Park and Eldora fairly economically. You do what you have to do