You will have a blast!
A few things to consider:
1) Forget about the lottery and go northbound (NOBO) from Horseshoe meadows. This strategy adds ~22 miles to the whole trip but permits are very easy to get in advance (look for Cottonwood pass/lakes at recreation.gov).
2) Starting in mid August is best - virtually no snow and mosquitos, dry trail and low chances of T-storms. If you go NOBO, even first and second weeks of September will be relatively warm since you will be finishing the final sections of the trail at lower altitudes.
3) Another advantage of going NOBO is that the trail gets easier at the end, when your legs get tired, and the meals at Vermilion, Reds and Tuolumne taste better!
4) Don't skip Vermilion - they are awesome! I spent nights at Vermillion and Reds and Vermilion is infinitely better.
5) I don't have any experience with resupplying on the JMT (done it 3 times unsupported) but, as far as I know, lots of NOBO folks ship resupply packages to Mt. Williamson motel and then pick them up by making a side trip via Kearsarge pass (~14 miles round trip form the junction to the Onion Valley TH; hitch to Independence). MTR and Vermillion are two other popular places to resupply.
6) Consider bringing a fishing rod.
Cheers
Last edited by Anton; 11/28/19 01:46 AM.