You can't *really* maximize the dining plan.
You can choose Goofy's dinner as the character meal you get on the voucher, instead of, say, breakfast at some other character meal, which gives you a couple extra bucks.
The only other way to maximize it is to plan what you're going to eat and what denomination voucher you will use, so that you will neither lose money by spending UNDER the voucher (no change given back!) nor lose money by having to pay OOP *over* the voucher.
There ARE people who like the dining plan.
But really, it's more of a pre-payment plan than anything else, and I pre-pay for meals and souvies by buying and earning Disney gift cards, which I then pay with for almost everything (not all the ODVs can take cards).
If you can stay on DVC points, go for the GCH.
If you don't want to spend scads of money, stay offsite. I
personally don't see the value in spending hundreds of dollars for a bedroom. Even for our honeymoon we were sure to get a bargain rate at the Westin Grand in BC before our as-bargain-as-possible Alaska cruise. Spending as much on a room as one could for a bed itself doesn't make us happy. So we like the HoJo, especially b/c now they have Westin-style beds.
Halloweentime is fun, even if you don't do the extra party over at DCA. It's all decorated and it's really cute.
We don't book tours of So Ca, mainly b/c my brother and SIL live in San Diego and will show us around anyway. Gray Line bus line has tours, where you pay for ticket plus the trip, or some other parks (seaworld, I think) you just pay full price for a ticket and get transportation for free. Definitely worth looking into!