Quote:

"I'm curious why people would regret sending themselves boxes? Or is it that they often send too much stuff?"

Too much stuff is a small part of it; no biggie unless you're on a tight budget, you just put the excess in a hiker box.

The wrong stuff can be part of it. Folks think they know what they'll like but find that they're sick of that after a while and are leaving stuff in hiker boxes and buying other food to replace. Certainly not all the time; on the PCT I had too many boxes, but was generally satisfied with what I sent to myself.

The biggest issue is being tied to going in to specific towns, and/or tied to the hours of the post office or business establishment where the box is waiting. For example, in the Sierras on the PCT I pushed my pace faster than I wanted to in the snow to barely get in to a town in time to get a resupply box. But I'd pushed hard enough that I ended up taking a zero anyway just to recover a bit. This sort of thing happened more than once.

On the AT there are so very many places to resupply that you don't go to them all. So imagine that you're hiking with someone whose company you enjoy, and they're going off trail in town X, but you have to split with them as your box is waiting in town Y.

Buying along the way gives flexibility.

I'm not trying to talk you into or out of anything here, just sharing ideas. Have a good trip however you do it!