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When doing the math, remember that you can sell the asset (assuming you dont keep it the full term of the contract). While its hard to know what it would be worth when you sell, even a conservative resale figure helps the numbers work.
Contracts that have been on the market for a while typically mean the seller wont budge much on the price - and it was potentially overpriced when listed
An effective strategy could be to start with a smaller/cheaper contract and add-on when/if prices drop..... it hedges your risk of paying too much for a mega contract.
The same use year on 2 different home resorts is still very helpful at the 7 month mark. much easier to combine the points for your reservation once the home resort advantage is irrelevant (with less than 7 months to go until your trip)
I would pick the resort youre interested in with the latest expiration date. Even if you are done with florida vacations in 2042, A resort with an expiration in 2057 Would presumably still be worth 5-figures on the resale market..... compare to an expired contract worth $0