The idea of pack inspection should be standard protocol. Far too often the "present yourself to your leader..." requirement for tenderfoot is a one-and-done (as are too many of the requirements). Every activity, outing etc... should include this at the beginning. When we begin to look at advancement requirements as a method instead of the aim, we begin to provide a scouting experience which mitigates so many problems often experienced and described on the forum and elsewhere.
Inspecting gear with scouts present, able to correct deficiencies, and looking for cleanliness, compliance, and serviceability is totally acceptable and expected. Done on a whim, in secret, or as a good idea is not what we want scouts to emulate. This inspection is best done in privacy as easy as behind a vehicle with the parents at the pick up point. They can take the prohibited stuff, have knowledge of what the scout has, and in semi-privacy, stash the polka dot drawers without having a public showing.
That is correct. June 1 (or the end of school, whichever is later, for those schools that don't end until after June 1) is the date that one program year ends and the new one begins. On that day, Lions become Tigers, Tigers become Wolves, etc. (in the Scouting sense, of course. Not in nature. That'd be weird.)
That means that in your example, a Cub Scout who will be entering First Grade in the fall would be doing summertime activities to earn the Tiger summer pin. If they will be entering Second Grade in the fall they will be working on the Wolf summer pin over the summer.
My $0.02 worth - I would go with the GG pack. Partly because of the weight savings, partly because smaller pack prevents adding unnecessary items (which saves more weight), partly because of the questionable stitching. Mostly because Im a gear geek and enjoy trying out new stuff.
Ive carried a GoLite Pinnacle on 2 treks (and a bunch of other week-long hikes). THe specs put it at 70 liters and 30# weight limit. My personal gear was right about 18# so very similar to yours - add Philfood, water and tent and I was about 35#. That pack was comfortable at that weight. It was full to the top at our biggest food pickup but everything fit.