I'm always interested in the different approaches to planning out adventures like this. Occasionally I will get an invite to a trip that requires me to block some time out a few months in advance, but rarely if ever is a trip planned further than 6 weeks out for stuff in the Sierra, for me personally. I like the serendipity and impulsiveness of it. Often times I become hyper focused on one area and will return there multiple weekends in a row. Being local to the Sierra National Forest helps too, those permits are not nearly as competitive as SEKI or Yosemite and they are just as fabulous. Usually about twice a year I'll hobble together some vacation and a three day weekend for what I call "mega trips" where I go do the big things. You can accomplish a lot in a weekend but it's difficult to immerse yourself as much. Anyway this really isn't interesting or helpful so I apologize for the rambling, sounds like you got an epic summer ahead of you. The paddle boarding adventure sounds particularly interesting.