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There is so much excellent territory to explore in the Sierra, it's almost a shame to ever retrace your steps! The hardest permits to get, are invariably for the busiest trails. One of my favourite passtimes is doing a deep dive on High Sierra Topix, the ultimate compendium of Sierra hiking knowledge, and finding little gems that I can eventually string together into a pack trip that takes in all new destinations. I know this is a JMT forum, and we therefore talk about the trail, but it's just one thin ribbon through the mountains with endless opportunities in every direction. The permit lottery causes a lot less angst if you are at peace with a Plan B to try for a walk-up and Plan C to enter the backcountry via a lesser used trailhead (then it's impossible to lose, you just adapt). The focus on end-to-end travel will become a lot less important once you're in the backcountry, and with a little nav practice the concept of planning trips that follow trails also becomes optional.
Lange Jorstad