Considering adding on pts through resale, as they seem to be cheaper there vs. through disney directly.
Depending on the resort, absolutely. Weigh the number of points your buying, closing costs through resale (though negotiable), etc. and compare them against buying through Disney. Disney doesn't charge closing costs for add-ons.
Not quite sure whether it would be better to add pts at SSR (our current home resort) where all our 250 pts are now, or to add pts at say AKV or OKW for example.
If you want the 8 - 11 month booking window at a different resort, then definitely consider adding on at a different resort. Also, be sure you're buying enough points to make it worth your time. Adding 25 points here or there will require you to bank/use/borrow just to get a couple of days. If you don't mind split stays, that may be exactly what you want. Just thought I'd mention it, though.
Can anyone explain the pros/cons of having some pts at one resort and some pts at another? It's my understanding that one the resort where the majority of your pts are held would provide you with home booking rights. So not sure what the advantage, if any is, of having pts at multiple resorts.
For each resort, you can use the points you own there to book 8 - 11 months out. So, the 250 you own at SSR can be used at SSR 8 - 11 months out, and if you pick up another 100 at OKW, those points can be used to book at OKW. You can't combine the two at 8 - 11 months out, you can only combine them at 7 months to make a reservation if they are the same UY.
Also, is it best to try to make sure the additional pts have the same UY as our current pts or does that not really matter, since you can bank/borrow if needed?
If you like your UY and can, I would keep the same UY. With Disney, they'll give you the same UY, unless you buy 160 or more points. Through resale, you can get whatever you want.
Having the same UY allows you to pool the points at the 7 month mark without having to transfer points. So if a night requires 30 points and you only have 15 available on one contract and 15 on the other, MS will just pull the 15 from both and make the reservation. Otherwise, you're in a transfer situation, and you can only transfer in or out of a member id once per UY.
There are definitely pros/cons to both. If you can't book at the 8 - 11 month mark, it really won't matter where you purchase. If you plan on making a large reservation (say a THV for several nights or a GV), then buy at SSR. If you want to be able to book at AKV or OKW at the 11 month mark every other/every third year (depending on the size of your add-on), then buy there, and try to find a contract with the same UY. If you can't, it's not the end of the world, it just makes things much easier.
Best of luck with your decision. I went through the same thing and purchased at VB, because we've had a difficult time making reservations there at the 7 month mark. Otherwise, I would probably would have just added more points at SSR.
