One question is - how much are you willing to spend? This is not a trivial question. If you are going to a timeshare (this is a timeshare site, you know!), you could check with the timeshare check-in office in advance, and see if they will hold incoming mailed packages. If they will, you can mail things to yourself, C/O the timeshare. Check with the timeshare the day before you leave, to see if the package(s) have arrived. If so, you don't need to pack those items. If not, you do. Obviously you want your meds with you, but you can pack lots of other things clothes, kitchen items, bath items, ect. Keep the boxes, and mail them back the day before you leave.
Now this costs money, are you willing to pay for this convenience? That's a personal choice. I do, (Bay Club has this service) and it saves a lot of stress. Just an idea. . .