Just wanted to comment on your title "Resale or New". It implies that if you purchase from Disney you get a longer expiration date. The expiration date is exactly the same no matter whether you purchase from Disney or on the resale market. For example, AKV contracts expire Jan 31, 2057 no matter how you purchase them. SSR contracts expire Jan 31, 2054 and BCV, BWV, HHI, VB and VWL contracts expire Jan 31, 2042 whether you purchase from Disney or via resale.
The only odd one out is OKW. There are two types of OKW contracts, extended and non-extended. The extended contracts expire on Jan 31, 2057. The non-extended contracts expire on Jan 31, 2042. The vast majority of OKW contracts on the resale market are non-extended. Disney sells only the extended contracts. So if you wanted to purchase an extended OKW contract, it will be difficult to find one other than through Disney.