I'll probably dress up again this year. I think its fun. Last year while DH was out with the kids, I put on my Lady (Lord & Lady type, not Lady & Tramp!) and surprised the kids by being in costume when they came back. It was fun, and our oldest DD & I went back out so she could do more trick or treating.
Here's a picture of one of my favourite Halloween's when we were at WDW in 2006.
Usually I make the kids costumes, and those Canadian royalty ones I made. The kids actually is based on Disney princess pattern, with Snow White style sleeves and Cinderella style skirts.
Here's one of us as pirates. Our headscarves are canadian maple leaf pattern
I like sewing costumes outfits, so I'd want fairy godmother to use her power to do all the housework, get all the supplies I'd need and give me an extra couple days to make the costumes myself

that way I get the enjoyment. And I would make the whole family gypsies!
btw a big part of why I started sewing for the kids, is that the store bought ones are not designed for the cold weather. Some years we have snow on the ground for Halloween, so kids have to be able to wear a winter coat or a couple sweaters under their costumes. This year one is a fairy, but she'll have long sleeves and pants with a skirt on top!
Eeyore's Butterfly - hope you feel better soon
NCTink - hope your dad recuperates quickly
pjlla - I hope you find the fun in dressing up! I made a stew in the crockpot the other day, and its a hit with the kids (last year they didn't like it). I made a low-point vegetable beef stew. Just a bit of beef, beef broth, some potatoes, carrots, green beans, wax beans, peas and corn. I think it came out to 4 points a bowl.
shewelch - great family picture!