I will say the same things that everyone else has, namely buy where you want to stay.
A long time ago (When they were building Hilton Head I saw the buildings going up) I bought at the Disney Vacation Club, because that was the only option.
I got married, and baby #1 came along. Time for an add on at animal kingdom because giraffe!
Then came the wanting to go to the beach bug. Trying to go to VB in a busy time isn't going to happen without VB point, so another add-on.
Now we are looking at having to go during school vacations, and want monorail, so we are looking at another add-on!
We have friends that bought saratoga,OKW, and Hilton Head.
They always want to trade points for VB points for some unknown reason!( Right its the beach!!)
The friends with kids want to trade for Animal Kingdom just for the Value rooms.
We have traded to get a treehouse. Other then that we go to the resorts that are home usually.
(I always look at the 7 month for upgrades! BC for DS 6th birthday!)