I've done both....MYW dining "free" in September at POP and just bought the DDE.
so..
1)both plans include CS locations
2) If you hate constant reservations MYW dining isn't for you. I know you have to make ressies sometimes with DDE but it is your choice. You don't lose out if you don't. I mean you could always use your TS at a restaurant that isn't as popular but it is a lot of planning.
3) Different "rules" at different locations can be (not always) but can be frustrating at times on MYW. These are non-Disney locations such as Wolfgang's Puck Express for example that will not allow you to drink bottled water for your meal even though MYW dining states "beverage". We ate breakfast (because we often shared and had tons left so breakfast wasn't a loss!) at Kona Cafe. KC is a TS. TS are appetizer, entree, drink and dessert. I understand the no dessert at breakfast. I've heard that Disney has changed their breakfast wording since I've been. But I was only allowed an entree for my TS no appetizer such as a grapefruit/ fruit cup etc.. I wasn't angry ....I just found these different rules very weird. And before you say "just don't go there" these strange rules seemed to be at some of my favourites....WP express, E of S, Kona Cafe.....
4) If you don't drink alcohol and you don't do a lot of sitdowns it might be hard to have any discounts beyond the $50 you spent on the DDE. That is my experience so far.
5) Snacks are the "vouchers" that are least used. I loved them. Ate grapes and other whole fruit every single day and more and they were gone early.
6) Sometimes you might forget to use your DDE. Sorry maybe that is just me but I forgot three times at CS locations on my last trip.
7) MYW dining is a lot of food but we shared all the time (didn't do many buffets) so that allowed us to use some for breakfast if we wanted or to make up signature (2 vouchers) dining. But we could share most meals using the DDE and not come close to 75.98 for the two of us in one day. Not even close.
8) MYW dining allows you to feel quite spoiled. I think that is the nicest part. I hadn't been in a sitdown restaurant in years. I scrimped to go to WDW. So it was wonderful feeling. I really enjoyed the variety and opportunity to just go to a restaurant and order whatever my little heart desired!!!
9) I have
DVC now. For me that will mean that I will make use of the kitchenette/kitchen. Yeah!! Sometimes I get tired of eating out. So if you are like me, like to eat in on vacation, I think the DDE is much better than MYW dining. I know there are a lot of people who do not like to cook/eat in.
So I loved MYW dining....but it was "free" and really "free" b/c my rack rate at POP was only $77. Plus, tip was included. But I hate reservations so I would probably never pay for it. DDE....well for me it's a wait and see....if I can remember to take the darn thing out....plus I do mostly CS so I am not even sure if I'll break even.
I am going to WDW soon (solo) so I'll have to check out the lounges/bars and spoil myself with a drink too. That's a nice feature with DDE. You can eat/drink in the lounges and get the discount.
One thing is for sure. I love that DVCers and DVCers with APs have options.