No one here can give you the answer as to what is best for you (or your boss) to do. All we can do is tell you what your options are. Then you have to fill in the data as it pertains to what you want. Obviously, the TSS has any size contract for any resort. If they don't have exactly what you want, tell them what it is that you want and they will eventually get it for you. What you should pay isn't exactly rocket science but, at times, it does approach rocket science. If a contract is "stripped down", i.e. this year's points already used up, then that needs to be considered. Do you pay this year's maintenance fees, etc. What deals are Disney offering. Things such as these need to be considered. For us, when we were buying, resale was a much better deal so we bought through TSS and had a very positive experience.