some of this depends on where he will be, and what else is going on.
if he is headed to college or grad school, or in town, he might not need anything, if he has judgment to skip the trip if conditions are terrible. (usually for a couple hours. they are pretty good on clearing snow)
if, on the other hand, he will be out in the boonies on call and has to get to work, a good set of snows are required. (you can just order them delivered to him in PA from tire rack mounted and ready to go...) the slightly skinnier ones would be slightly better in snow, but worse on dry roads or ice. (my humble opinion)
if you really want him to be prepared, you can get a set of chains and make sure he knows how to use them, but they are likely better left in the trunk.
the 507 00 vw spec 5w30 will be fine.
( I drive to PA to ski several times a year and she always starts fine, at ten below. just have to wait that couple seconds for the glow plug light to go out.)
might want a new battery just for the heck of it, if it is the original.
if you really want to show him the love, take care of DSG service and timing belt if it is anywhere close to time, before he goes.