New sneakers! I have arthritic knees and I always get new sneakers a few weeks before a trip. I find bringing 2 pairs of sneakers, my new and the slightly older pair to be the key to my success in never getting blisters and keeping the knee pain kind of in check. Timing wise, I will stretch out a pair (like, right now I'm due for a new pair, but, I'll wait until January to prep for my Feb trip) if I'm trying to save a few bucks. I buy new sneakers about once a year regardless.
I also bought a bunch of first aid things our first trip, and didn't need most of it. Ponchos, absolutely. I have yet to use them, I call them my lucky ponchos now, since if I bring them, it won't rain!
I did get a new tinkerbelle shirt for my girls trip this Sept, that was a fun splurge. A dollar store hamper was a must, and we started using it while tent camping, too.
I buy a buncha groceries and a box of good wine to put in the checked bag. (before anyone freaks, yes, I triple bagged it, no it didn't leak, and one would have to be an idiot to not know to wrap up their wine properly).
Other than the sneakers, which I get at fleet feet for a pretty penny and consider a medical need rather than a want, there isn't much I buy. This is still you, just on vacation. You'll look great in pictures with your favorite clothes on, no need to buy new. A laptop wouldn't be used much, I wouldn't bother. A concierge at your resort can handle the same things you would turn to your laptop for. Your luggage is FINE!! If it looks a little rough, people would just blame the airline handling being too rough. I am comfortable in my own skin and with my sometimes older things, so maybe that's the reason why I didn't feel judged while at Disney. Or, possibly, everyone is too busy enjoying the magic to judge other's things. Just show up as you are and have an amazing time. Save that money on the new stuff and put it toward your next trip!
