We own a four resorts and three use years and like the setup so far...
Here is how we did it:
350 VWL (250 primary, 100 add-on) Feb
100 HHI add-on Feb
180 BCV add-on Feb
100 OKW resale Apr
270 BCV Second new contract Aug
We feel that the Feb and Apr are a bit too close together for multi use years making the admin/banking/transferring issues fun. Most times it is not an issue, but if life is busy and I fall behind on the details I fumble a bit... We just added another 270 on at BCV for an August use year. We did it this way so the two big contracts were six months apart. If we are going to bank at the six month window the next contract is refreshing itself. I am probably not explaining it well, but what is new...
I think I can say we are done. If I buy any more points, Disney better start padding the rooms with rubber and provide white coats...
Another note, the smaller contracts are great. One little "gutcha" is; if you are booking a reservation for a non-home resort within the seven month window and have plans for a home resort/11 month ressie later in the year, be specific to MS which points to use. If they just pull from any account you may be short if you want to stay at a specific place.
Example: You have a primary 150 pt @ WVL and a 125 pt add-on @ BWV. At the 7-month window you call MS to stay @ OKW requiring 115 pts (made up point cost). MS pulls the 115 points from your account. In January you call MS at the 11 month window to book VWL for Christmas. When you make the ressie, the MS rep may say "Sorry you only 35 pts for VWL". This is because the prior ressie, they pulled from VWL leaving you with the BWV points. Most reps will ask which resort you want to pull from. At times we had to be very specific to prevent from being SOL. It actually just happened. The MS rep did some magic am did some shuffling to fix it.
You can do it, no horror stories.
Good luck and have fun!!!