Cody, maybe in your case, the $259 would be worth it...
Buy I invite family and friends, and so will need 1 or 2 day passes to give them, and with the MYW tickets, the cost is going up.... up to $60 at the highest.
I have some old, unused tickets that are worth around $30 / piece. So I'd be trading in approx tickets for 2 days, to get 1 day of the new stuff, which may or not have park hopping on them, or expirations....
I decided this, by taking all my old tickets to the Guest relations, and the person there said I'd be much better off saving my old tickets, and using them as fillers..... I suggest you do this as well, and they can help you decide whether it's worth it for you. I think the older the tickets, the less value you get for them, so it's better to use them, than to upgrade. If your ticket is relatively new, you get a better deal.
So I guess it depends on what you're doing, but basically the prices will only go up, as a general trend.
Goldi