As long as you treat them as separate contracts and pay attention to the banking deadlines for each contract you should have little trouble at all.
You can even use points from both contracts making reservations for a single trip at 7 months by reserving individual days from each contract and MS will just link everything together. In addition, you would be able to transfer points from one into the other (thus using your single yearly transfer for both accounts) to use the combined points for something like the cruise or other non-DVC reservation at 11 months. You would not be able to use ALL of the points at either resort until you reach 7 months before arrival.
We have four separate contracts, with 4 different Use Years at 2 different resorts and have used a checking program to track the contracts by setting up a separate account for each within MSMoney. Better yet, Caskbill now has an excellent DVC Tracker program available on his website - with the final upgrade coming out soon. I also have MS confirm my accounts with each phone call.