Unpopular opinion: I quit planning food drops months ahead after a guy on the AT told me he just resupplies in town
I used to map out every food drop for a 3 week trip like 2 months early, weighing out bags of oats and peanut butter on a kitchen scale at home in Columbus. Last June I ran into a hiker outside Damascus and he said he'd never mailed a single box in 4 thru hikes, he just walked into whatever grocery store was in town and bought 4 days of food at a time. I tried that on a 9 day loop through Virginia and honestly it was way easier, I spent about $70 instead of the $140 I'd have paid in postage and shipping. Now I only pre-pack for stretches longer than 6 days with no town. Do most of you actually mail boxes or just wing it at the store?
Town resupply works great on popular trails where stores are close and well stocked, but out west on the CDT or in the Sierra it falls apart fast. You can hitch 30 miles into a town with one gas station and find nothing but chips and energy drinks, then you're stuck. Mailing boxes still makes sense for those long empty stretches, so it's less about one way being better and more about where you're hiking.