KIS - This is one of those very difficult WDW decisions. LOL I struggled with this same thing for well over 2 weeks.
Here's exactly what I did -
First I did a very rough outline of each day. You'll want to include anything like spa treatments, golf, watersports, babysitting, or anything else you plan on doing. This is hard to do if you don't have park hours and such and of course it will probably change a dozen times before the trip, but try to get a pretty good idea of what you want to do and lay it out, including the approx. cost of those side things. You'll also need to include tips and taxes when needed. Like you probably would want to tip the spa person, at least I do.
Next I laid out a rough outine of places we wanted to eat. Yes, you need to pay for the silver plan for everyone, but you can pay cash for him/her and use their wishes on something else. Again, I used
www.wdwig.com to look at menus and figured out costs, sort of guessing what we'd probably eat. I also included 20% tip and 6.5 tax.
Then I tallied it all up and came out ahead doing it on our own verses the plan, because we knew we would not be eating 2-3 large meals a day, you're not as hungry when it's hot out, at least we found that to be true. Plus we like to snack on little treats during the day. We also found that we were just so wore out, we'd end up just grabbing something to eat anywhere. We ended up cancelling a lot of our PS ressies.
We've been to WDW well over 30 times and each trip is so different. This time we have our 3 year old along, so we will only be doing 2 character meals and 2 nice dinners. We don't plan on using the babysitting, knowing us we'll be way too tired by the end of the day to get dressed up to go someplace nice. LOL
We also won't be using the spa, golf, water sports and such. A while back someone took the time to post a pretty complete list of things you can use your wishes for, maybe someone knows the link. So if you had left over wishes, remember not to waste them, use them to get gifts.
I know this plan is great for some and for others it just doesn't pay. If it was just my oldest DD and my hubby and me, we'd probably do the plan because we'd do a lot of the extras and eat at places like V&As, Cali Grill and the like, but this time we're not so it didn't pay.
If you do go with the plan it won't be as much of a wing it trip, but you'll still have a ton of options!
Good luck deciding! Take your time and don't rush into deciding, you can always add the plan at a later date. And remember which ever way you go it will be a wonderful trip!!!
Pam