I did little planning. I think the biggest thing is to buy gear strategically beforehand. I can help you with that, if you want (I did the Trail last year). Food is never an issue & I ate cold food until Damascus. The question is how much you can deal with. I always fly by the seat of my pants, but if you have to eat a particular type of oatmeal or something, little towns along the way might not have some of the stuff. Gear along the way was never an issue, as there are tons of places (although sometimes you have to get a bit creative). Also, after 30 miles, you don’t need a GPS, but eventually, you’ll need either the Wingfoot book or both the mileage book & ATC book, b/c there comes a point where you can no longer rely on others to ask where the water sources, next town, etc. are. You can buy that though (and all the other gear you realize you need) 30 miles in at Neels Gap. I’ll be doing Georgia starting around 5/24, so maybe see ya out there.
Shera, Princess of Power