I’m in a bit of a rush here to get out the door, but I wanted to add my perspective fresh from this years thru-hike.
May 14th - Not too late at all as long as your confident that you’re going to do big miles. I met (and was passed by) lots of people who started as late as May 18th (I started April 23rd) and they had no problem finishing. But then again, they were also the kind of people who consistently did upper-20 miles and had quick in-and-out town stops.
If I had to do it all over I’d carry just a tarp for the whole trip until Washington when I’d switch to a tent. The tarp alone is plenty fine for almost all of the desert, because if you’re like most, you’ll find that cowboy camping (sleeping under the stars) is much preferable to tarp/tenting for most of California. I will say though that getting a bug bivy sent to you in Kennedy Meadows should be a definite.
Bear Canister: didn’t know a single person this year who carried one the entire way- or really any longer than Sonora Pass/Echo Lake. They aren’t as bad to carry as they’re oftentimes made out to be, but its still 2lbs. which you don’t need for practically anywhere outside the Sierras.
Rocham