On my last trip to WDW I was pretty focused on allowing my mom to experience her favorite attractions along with anything new that she hadn't seen. We didn't spend a lot of time looking for characters or stopping to watch street performers.
Mom expressed interest in meeting more characters this time and I happily agreed with her. I'd love to find some of the characters that I haven't ever met before. Sadly, WDW entertainment has cut down on how many characters you see out and about. You also won't see some of the less "popular' characters around doing meet and greets anymore.
While reading my 2010 Unofficial Guide I found a really cool website that tells you where to go at what time to find character greetings as well as street performances. This guy updates the website every week and puts lots of information on it and is really well organized. Now, he can't specifically tell you what character will be where at what time but he informs you of your best shot of seeing them. Here's the link --- http://pages.prodigy.net/stevesoares/
If you have a specific character that you or a family member wants to meet you should check with Guest Relations at the front of any of the four main parks and they can try and track down where you're beloved character will be that day. I haven't done this myself but i've heard of people doing it.
I have a strong desire to meet Hercules characters. STRONG desire! Unfortunately for me, Hercules and Meg don't come out anymore and the only time you'll even be able to SEE them now is during Fantasmic. The villain I most want to me is, ironically enough, from Hercules. That'd be my buddy from the underworld... Hades. He's a comedic genius!
When mom and I will be at WDW this year they have the Food and Wine Festival going on. They have a concert series called "Eat to the Beat." For the days that we will be there we've got three performers we could go see.
Richard Marx September 28-29
Starship Starring Mickey Thomas September 30-October 3
En Vogue October 4-6
Mom really wants to see Starship and I would LOVE to see En Vogue. I grew up listening to En Vogue and thinking they were so cool. Oh! And hey! Kelly Clarkson performed with them back in the day! Woooo! Free Your Mind!