Great photo. I laughed a good one!
I've looked into and considered the Lake Chelan trip a few times. It sounds like a lot of fun catching a ride on The Lady of the Lake and getting dropped off somewhere to begin a hike. I've never done that hike but it's my understanding that it can be very hot and dry especially in Sept and in addition to bugs you have Rattle Snakes to contend with. It's a much more arid and dryer environment then the west side of the Cascades. In fact, my North Cascades guide book recommends it as an early season hike for those reasons. I also looked into the Alpine Lakes area. The photos I've seen look spectacular. It sounded like one of the most crowded areas of the Cascades. It's one of the closest to the Seattle metro area and many of the lake camp sites required a reservation in advance just to overnight camp. So that for me killed the Alpine Lakes area. I'm saving that one for some time in the future when I can do a late season hike after all the kids are back to school. Late Sept or early Oct would be ideal.
Decisions, decisions. The Olympics in early September would be a very nice place to escape the summer heat. Lots and lots of shade. When I was there last Labor Day weekend I was very pleasantly surprised at the lack of crowds. Once I got up the trail beyond 6 or 7 miles there were very few hikers. I don't know if you are driving out from MS but there are endless possibilities. Hmm, the Bob Marshall Wilderness or Glacier NP in MT, Sawtooths in ID, Wallowa Wilderness in eastern OR, Trinity Alps in CA.................
So many trips, so little time.