Planning an 8 day JMT hike starting off at Taboose Pass and ending at Whitney Portal. Started "lurking" to see what intel I could gain

Mainly concerned about shuttle or parking from one trailhead to the next. How much exertion to anticipate heading up Taboose Pass, and if night one at Bench Lake is too ambitious. And also, considering how much snowfall there has been, if microspikes are enough, or if we need to bring more than that (late June adventure).
Cheers!