I did it in September last year, and it didn't rain on me but for about five minutes close to the southern terminus. Most of your gear looks great to me, but I'm worried about your shoes. Even tough vibrams could leave your feet feeling battered if you're moving 20 miles in a day, especially through desolation. I used an odor-blocking nylofume bag with no bear can, and didn't have any problems for my own part.
If you do a bpl search, you can find several great threads on the TRT with links to simple tables folks have compiled about water sources; the north is definitely the driest section, but the northeast isn't great either. I usually had extra when I rolled in to the next water source, but I carried a bit and also found I could hike pretty well without drinking a whole lot if needed to.
As for the scenery, it surely isn't spectacular all the time. Desolation is definitely the nicest spot, but it doesn't offer any views of the lake proper where the TRT goes through it. On the dry, dusty, boring northern and eastern sides, you get frequent relief with great views of the lake, and sometimes you'll pop over a ridge or hit a peak that gives you great views away from the lake as well.