I did the number crunches when i went and to me the Dining plan constricted me too much and didn't seem like I was going to save any money with it. I could see this helping out if you have kids but for just two people eating I didn't see a money savings in it at all. My main issue with it is there isn't a lot of flexibility in where and what you can eat so if you wanted to get something not part of the plan you would end up spending money on food anyways. I would look at Tom Brickers site though for lots of helpful hints in regards to the dining plan. I posted it below.
Thanks, I appreciate the resource. I read many articles like that one and my husband seems pretty set on doing the dining plan. I could go either way. We looked at menus and decided it'd cost us perhaps less a day or two, but probably more the other days based on what we would buy. We would want to do a sit-down meal each night (that's part of what we are looking forward to), and whether or not we got the dining plan we would have to reserve a table months ahead. So i don't think it's going to 'force' us to do/go/order anything we wouldn't have anyway. If it was just up to me, I'd probably opt out in favor of a little more freedom. But money-wise, I think we'd spend close to the same with or without the plan.
I usually bring a small backpack with me. I find that more comfortable than having a purse on my shoulder all day, and it gives me a place to stow my camera, sunblock, kleenex, light sweater, rain poncho etc. You can just keep it on your lap on the more tame rides. The bigger rides all provide a place to stow your stuff, either in a secure net on the ride vehicle or in a little cubby on the loading platform. There might be one or two rides (like maybe Space Mountain, I think?) where there isn't really a designated spot, but I just put the bag on the floor with the strap around my leg, and that is perfectly fine. All you really need to worry about is remembering to take off your hat or sunglasses so they don't fly off
All Disney transportation within the resort is free, and if you stay in a Disney hotel you'll get a free Magical Express bus ride to and from the airport. Fastpasses are also free - anyone with a park ticket can get them. I say this because I have often overheard comments from park guests who think that you have to pay extra to get Fastpasses, but that is NOT the case.
I would highly recommend getting the Birnbaum Official WDW guidebook and reading it cover-to-cover. It will tell you pretty much everything you could possibly need to know.