I think your confusion comes from an underspecification of the initial problem. Are only your memories reset, leaving more subtle personality or physical changes in place (Where did this tan come from?!? Why am I so relaxed?), or are your brain and body (and the rest of the world) entirely reset to the way it was before you went on the vacation? Really, the problem doesn't specify what it means by "not remember the trip" well enough.
Part of what prevents me from understanding the riddle is that I believe vacations are worth more than the memories and photos: vacations change you.
Not if everything is reset back to the way it was!
I think the problem is meant to imply that there would be no way of ever telling you were on the trip; if you took a vacation and then afterwards your body and mind were reset to the way they were before the trip, as were everyone else's, and all evidence of the trip was destroyed, would you take it? Your list of vacation features are all things that, to me, are implicitly implied to be reverted back to previous settings after the vacation.
Isn't there a medical condition that makes people forget the waking period after they go to sleep, and so begin the next day with a mindset (progressively) falling behind the world? Suppose you offer someone with this condition a half-day-long experience which would be as worthy (considering their actual goals) as anything they would ever have a chance of doing, if they agree to forget it immediately?
How much is half a day worth, if you only have a day, yet are reasonably certain you'all be around tomorrow?
I don't think I understand the riddle of experience vs. memory. I would daresay that means the concept is half-baked.
Within the TED talk, Daniel Kahneman poses the probably familiar philosophical quandary: if you could take a beautiful vacation and afterwards your memory and photo album was completely erased, would you still do it? Whether you would still do it illustrates whether you live in service of the experiencing self instead of the remembering self.
Part of what prevents me from understanding the riddle is that I believe vacations are worth more than the memories and photos: vacations change you.
Maybe you could argue that this change is also a form of memory in service to the remembering self, but I'm not sure that's what he meant. In his thought experiment on vacations he asks if you would still take a vacation if, at the end of it, you forgot the whole thing and all of your photos were deleted.