1. Besides Couch to 5k, I really like Jeff Galloway's beginner program. The "run" days are actually run/walk days.
http://www.jeffgalloway.com/training/5k.html
Runner's World has a good 8 week program
http://www.runnersworld.com/article/...-1X5-3,00.html
2. Get some good shoes. You can go to a running store and have them fit you. I haven't had the best luck with my local running store, though. You can also use this to get an idea about what type of shoe you need:
http://www.runnersworld.com/shoeadvisor
You can order shoes from Road Runner:
http://www.roadrunnersports.com/
"More expensive" isn't always better, BTW. I wear $65-$70 Asics that work better for me than many more expensive shoes have.
3. Get a shuffle or an Ipod. Music or podcasts makes it all easier.
4. You won't have to raise money to run a 5k. There are dozens of 5ks every year in every major city. They usually charge $20-$40 for a race and have different benefits. You usually get a shirt. Sometimes you get a ribbon or a finsher's medal. Your local running shop will have flyers and may have a website that lists local races.
Here's an example:
http://www.fleetfeetstlouis.com/calendars/races
There's a ton of race calendars. Just google race calendar and your area and you'll find one.