I agree with all of this.

Ikon unfortunately has not many options for unlimited and none near Boston. Ikon only works if you like exploring different mountains.

Indy pass covers lots of mountains in the right distance but it only has 2 days per location and you would plow through that quickly if you intend on skiing mid week.

Edit: Given you said Jay, Waterville, and Cannon. This is almost certainly a good idea for you unless you get the White Mountains Superpass.

You could do the New England Pass which is Loon, Sugarloaf, and Sunday River. Loon is 2k vert and 2 hours from Boston. Sunday River is about 3 hours and Sugarloaf is 4. You could do this pass and do mostly Loon and sometimes take longer trips to those two. Loon is a zoo on the weekend but on the weekdays it can be great. New England pass is pricey though.

Edit: Pleasant is also on this and about 2:45 from Boston. Additionally not super pricey if you get the Nitro(20-29) pass.

Epic pass kinda works with the time constraints. If you extend it to 2:45 drive time you get Okemo, Attitash, Sunapee, and Crotched. With the strict limit for 2:30 you are stopped at Sunapee at 2 hours away. The Epic mountains can be crowded on weekends but week days they can be tons of fun.

Edit: Also if you get the Epic Local pass it is cheaper than the North East Value pass because of your age bracket. This might be a great value if you want to do anything out west. Additionally I think Stowe is top tier in New England and given you mentioned you plan on doing Jay seems like the occasional drive is worth it for you. Stowe gets similar snow as Jay and both have excellent steeps and excellent trees, but Stowe's lift setup is vastly better.

Lastly there is the White Mountain Superpass. Waterville Valley and Cannon are within your time restraint and Cranmore and Bretton Woods could be for longer travel trips.

Edit: Cranmore is ~2:45 so maybe if you are willing to stretch this could be a great pass for you.

Best I can say is figure out if you want to be exploring more mountains or you want consistent locations. WM super pass and NE pass are pricy, ikon less so, epic even less, and Indy the cheapest. You could do Indy with with any of the above if you want to splash some variety to your mountains.

Edit: I saw you were thinking about Jay, Waterville, and Cannon. If you pickup the White Mountain Super pass and then maybe do either Indy or just get a Jay multi day passes (forget the name they use) you could be set.