I'm Kumiko, and this'll be my fourth year attending. Sakura Con was my first convention, and believe me, you're going to have a blast, especially now that we're moving to a larger location. I'll be part of two CLAMP groups, going as Fuu Huouji from Magic Knight Rayearth and Princess Tomoyo from Tsubasa: Reservoir Chronicle.
Oh, Club Sakura's the best! That's our rave/J-pop dance, and it's always a ton of fun. One of my best friends was in charge last year, and I think he's doing it again this year. They play a nice mix of anime themes/music and electronica, and they usually have anime music videos playing on the big screens in the room. Wear a comfortable costume, though, because it gets hot and very crowded in there.
We've had a concert with a J-pop artist the past few years, so I'm guessing that tradition will continue (haven't checked out the site to confirm, but I'm pretty sure it will). Definitely attend, as it's well worth the experience. I wasn't able to make it last year, but I attended the Hiro concert the year before and it was a blast, especially when she sang "Fly Me to the Moon" at the end and everybody sang along.
The cosplay skits are always worth seeing, such a range of creativity! Get in if at all possible, you won't regret it.
The fashion show, held on Sunday morning, is a good thing to go to if you're really interested in costumes. I always enjoy that, and you get a chance to see some really nice cosplay on display.
One of the best parts, about any con, is just mingling. I spend a lot of time just walking around the halls, seeing everybody's costumes, taking pictures, getting mine taken, and meeting new people. I'll usually end up eating at least one meal at a con with people I've just met, and while you might not keep in touch afterwards, it gives you friends to look forward to meeting the next year.
Other great stuff: the anime music videos contest, karaoke (I watch, but never participate myself because I get massive stage fright), the anime dating game (so much fun!), and meeting voice actors.
Oooh, definitely try to meet at least one voice actor if you can! I missed seeing Ikue Otani (Japanese voice of Pikachu and Merle from Escaflowne) last year, and I've been kicking myself ever since, especially since Merle is my favorite costume! Scott McNeil, the American voice of Kouga (Inuyasha) shows up quite frequently, and he's a great guy to meet. I've also met David Kaye (Sesshomaru) and Kirby Marrow (Miroku) at nearby cons, and I loved it each time. Try and find out early if an actor from a show you like will be there, so you can have something decent for them to sign. I got Kirby Marrow (who's pretty cute, by the way, check out my Anime Evolution 2005 gallery) to sign my Escaflowne wallscroll, since he's the voice of Van. Much better than just having them sign a slip of paper. I'd love to have Otani-san sign it as well if she comes back this year.
Anyway, just keep your eyes on the Sakura Con website to see what's coming up, since they should be posting a more definite schedule soon. Oh, and don't forget to bring plenty of cash for the dealer's room. It gets bigger and better every year.
Why yes, it is my natural hair color, darling!
Working on: Sakura/Syaoran/Tomoyo fall uniforms, Ashitaka
Ashitaka (Princess Mononoke); Sakura Kinomoto (Cardcaptor Sakura)
Autumn '08/Aki Con
Ryoga Hibiki (Ranma 1/2); Shura!Sakura, Jade!Syaoran (Tsubasa: RC); Kokon (Kon Kon Kokon)