Congrats! That's awesome! Disney will always be there but the wedding is so much more special. As for getting a decent pair of shoes, the great part about a beach wedding is you can find some fancy flip flops and a sun dress and a nice hat and be good to go. My BIL/SIL got married on the beach in the Bahamas. She wore a wedding gown but no long train and went barefoot, as did the rest of the wedding party. Dh & I were on our own honeymoon and couldn't attend but I would have loved to go. They had great photos with the sun setting over the ocean behind them.
Formal weddings are just so outrageous anymore. I don't know how people can think of spending $50k+ for a wedding and can barely afford a home.
Here's that faint smiley if you still want him

I think you'll be able to pick yourself up, start making a list of priorities, and start working on them.
For me, of all the things on your list, dieting would be the hardest.
As for Christmas, are you saying you would make one stocking and pick from a hat to see who gets it? That just feels unfair imho.

Why not just spend much less than $250 each? That way everyone gets a gift and it's still affordable for you. My parents have been giving us $100 probably over 25 years now.(3 of us) Once each of us were married, our spouses got one too. At first I was a bit sad to not have a thoughtful gift to unwrap but once I moved out, I really appreciated it and almost knowing we can count on that helps us out a lot.
Dh is one of 6 so his parents spent much less, usually a $50-60 gift card to a restaurant for both of us.
I would hate to think any of our parents are going into debt to give us large Christmas gifts they couldn't afford.