JHV, I had a whole long post that I apparently didn’t send in prepared earlier today, sorry.
Let’s see if I can reconstruct some of it.
First off, is he going to be in a dorm or in an apartment with other boys (organized separately, not part of the regular dorm situation). The reason I ask is because a dorm will provide things that the boys will otherwise have to buy if they’re on their own.
You don’t need to send anything like TP or tissue anymore. We have it here, even Kleenex tissue in a box. He might have to buy some of it on his own if he wants higher quality products. Yeshivas tend to buy the cheapest stuff available, which can resemble sandpaper, ouch! But good stuff is available at most of the local stores these days. Send a basic supply of toiletries so that he won’t have to go hunting for the stuff right when the zman gets going.
As far as food, there are tons of falafel stands/pizza restaurants that are to be found in most major parts of EY. A lot will depend on where his yeshiva is located. If it’s in the boondocks, then he will have to manage with yeshiva food and maybe have a stash in his room that he can tide him over when he gets hungry in the middle of the night. If he’s in the Mir or some other major yeshiva in Yerushalayim or Bnei Brak, there are lots of places close by that he can grab something even until pretty late in the evening.
Bein Hazmanim can be a little tricky, but it is different for guys. Are you bringing him home for Pesach? (I’m assuming Succos is too soon after the start of the year to come home). The Elul Zman ends the day before erev YK and then he will be busy right after with getting his Arab Minim and maybe building a succah by the dorm (don’t know how they work those issues). What will he do for meals during YT and Ch”M? The last week of Bein Hazmanim is the hardest part and a lot of the boys go on tiyulim. He should just be cautious doing those because unfortunately most accidents happen during those times.
As far as labeling clothes, I would since boys are not always the most organized and once you’ll get a bunch of boys together in one small dorm room (apartment sharing a bedroom is the same difference), so all of those black socks/white shirts, etc, will get all jumbled together. Make sure he knows how to do a load of laundry or find someone who will do it for him periodically. I think Mir has a dry cleaner who will pick up and deliver to the yeshiva, which is a big time savings for the boys.
BTW, don’t forget about the new luggage restrictions these days. Even El Al has gone to allowing only 1 suitcase weighing 50 pounds. I’m not sure what the prices are for the other airlines, but I had heard that El Al is allowing a second suitcase for $70 or $75 extra. Could be worth it since he’ll be going for an extended trip, unless he’s a really geshikt boy who will be doing his laundry weekly.
Well, I hope this helps. If you have any other specific issues, post them and we’ll see if we can help further.