Okay, guys, this is a tough one.
I currently have a AAA package booked for just myself and my officemate for 5 days/4 nights at the end of January 09 in a moderate, with 5-day parkhoppers.
My family is tentatively planning to take our son on his first trip to WDW in January 2010.
If I get a pass for myself, and my officemate buys a discounted 5 day parkhopper for herself, we can save about $250 on this trip using the new passholder room rates that just came out for January. I would cancel the current booking and rebook with my pass in hand.
I can also theoretically save more money on my family's room in 2010 if passholder rates come out in time for that trip.
The only drawback? The January 2010 trip isn't set in stone, and a lot can happen in a year. We might take the trip earlier, or we might take it later, which would waste half of my annual pass.

I am incapable of making a decision without asking. Any advice from you sage Padders?

Look at the total cost for the room and tickets if you keep what you have - vs- the total cost of the room, your AP, and your friend's hopper.

If the second is cheaper - no brainer, do it.
I suspect it might not be.

So what's the difference in the cost between those two? That, basically, is the cost of the 'gamble' you're taking by getting the AP.

To make your decision a little more complicated (what can I say, I like to help :D) Do you anticipate a number of Table service meals during your January 09 trip? What's your view on adult beverages? If the answer to both is 'yes' then you might want to look at the Tables in Wonderland (previously Disney Dining Experience) which gets you 20% off food and drink at most table service locations, and some counter service ones (like the one at POFQ). It costs something like $60, and is only available to Annual Passholders or Florida Residents. If you're doing the dining plan - never mind - it probably won't be worth it for 2 people and that short of a trip.

If the second is cheaper - no brainer, do it.
I suspect it might not be.
You're right about that, Cathy. The $250 saved is assuming I'm going to use at least 5 more days on my pass. If I don't, then I'd be losing money.

To make your decision a little more complicated (what can I say, I like to help :D) ...
We're not getting the dining plan on either trip, and I also anticipate very few table service meals on either trip. My officemate and I like an occasional adult beverage, but we're not big drinkers. I might have to work pretty hard to make the TiW card worthwhile.

I called Disney reservations to make sure they still have moderate rooms available for our dates using the new code. They do, but they're going fast.

If it were totally outside your control (say, if you were trying to guess if Mouse Adventure Fall 2009 was going to be in the same 'year') - then I'd say it's a pretty big gamble. (Not that my sister had to make that very decision recently or anything....!)

BUT, you're going again within the 12 months IS somewhat within your control. But it's not really the $250 you're gambling with (or rather, that's the upside to your gamble) The money you'll be OUT is the difference between the ticket you would get and this ticket, taking into account the discount on the room.

Littlej - Just to add my 2 cents . . . You have to calculate the increase in price to buy an AP over the 5 day park hopper, minus out the savings you'll get on this trip for your AP discounted room, minus out the savings you'll get on your AP discounted room next year AND minus out the savings for you since you will not have to buy another pass for the Jan. 2010 trip.

Without knowing these costs, I have to think it's worth the gamble to buy the AP now (other discounts you can use on this trip and next are free parking at all of the Parks if you rent a car, 10%-20% off some restaurants in the parks, shops and in DTD, discounts at the DTD movie theater and half price tickets to the WDW miniature golf courses [Fantasia and Winter/Summerland at Blizzard Beach]).

If your son is flexible with his school schedule (or is not even in school yet), you can probably schedule the Jan. 2010 trip within the first 3 weeks if you are going at the end of Jan. in 2009.

When we went last August for almost 2 weeks, we bought APs planning to return within the 365 days. We arrived on a Sat. in 2007, but didn't activate the passes by going to a WDW park until that Monday (which bought us a couple of extra days for this year). Also, although we were able to go a couple of weeks earlier than last year, we had the flexibility of saving our non-Disney activities (SeaWorld, Kennedy Space Center, DTD, shopping, etc.) for the end of our August, 2008 trip if our APs expired while we were there.

With careful planning, you can buy the AP and save a LOT of money. The only downside is that with the AP in hand, you'll constantly be scheming to squeeze in additional trips to WDW within the 365 days, b/c after all, you've got the AP paid for already ;)

With careful planning, you can buy the AP and save a LOT of money. The only downside is that with the AP in hand, you'll constantly be scheming to squeeze in additional trips to WDW within the 365 days, b/c after all, you've got the AP paid for already ;)
That's a downside?

It's a "downside" with a wink, wink ;) But, despite my best efforts to squeeze in a long weekend trip with one or two of the kids, we didn't get more use out of our APs except for our 2-week August trip.

It's a "downside" with a wink, wink ;) But, despite my best efforts to squeeze in a long weekend trip with one or two of the kids, we didn't get more use out of our APs except for our 2-week August trip.

My first year I got two extra trips in because of my AP. Thank Goodness Southwest flies directly for me!

I'm in the same boat. Going for MouseFest and SUPPOSED to be going again in September during DH's conference at WDW. However, with the economy the way it is, I'm not going to chance it. For me, it was too much of a gamble.

Kinda going along with what Tina said... don't get an AP if you think the next year is going to be filled with "possibly's" and the like. If you get an AP, it is best to know that you will go back again so that you can at least break even when comparing costs with a non-AP ticket.

Also, consider that very little inventory has recently been put into AP rates and the savings have been beat by other discounts, again recently. Obviously, we can't predict that for the future, especially considering the economy, but I hate to predicate the AP purchase on a future "definite" AP discount.

I, too, find the APs very dangerous! That "after all, I do have the AP" attitude gets me into lots of trouble ... but man, that's my kinda trouble!

Decisions, decisions!

Leslie brings up a good point about the discounts. While some may have been "traditional" at times (such as free parking) it does not mean that all current or past offers are going to be available for you during the time that you are vacationing.

After all, they do say that discounts and offers may vary and are subject to change and/or availability.

First of all, thank you, THANK YOU! to everyone for their great advice. I was literally ready to buy my annual pass, when I happened to see Mark's little note yesterday afternoon. I'm happy to say that we've changed our plans a little to take advantage of this deal, and we're actually saving some money. So I'll tuck away all this little information tidbits about an annual pass to use again someday. With my son turning 3 next year, I know we'll have plenty of opportunities to use them!