I've worn glasses ever since second grade and switched to contacts in eighth grade. I'll never go back to glasses.
I've personally never had problems with contacts being uncomfortable, unless they're old and I need to start a new pair. (I wear soft disposable lenses; they are the type you have to take out when you sleep.) I had a hard time getting used to them when I first started wearing them, but that's mostly because I am really sensitive to my eyes being touched. It took me forever to get to the point where putting on mascara wasn't a big deal.
Both my mom and sister have tried contacts and haven't had much luck with them. I think they both tend to have dry eyes and the contacts didn't help matters. My sister also has a similar problem with things near her eyes.
I find that contacts are slightly less expensive than glasses. My insurance treats them similar to glasses. They will either pay for a year's worth of contacts, or you can get new lenses for glasses. My insurance will pay for frames every other year. This year, I opted to let my insurance pay for glasses (needed a backup pair) and purchased my contacts out of pocket. I think I paid about 60 dollars for a year's supply.
The one big thing about contacts is that you do need a pair of glasses just in case. If you eyes get aggravated, it's a good idea to wear the glasses, as contacts can cause further damage. I managed to scratch a cornea in high school, and was stuck wearing glasses for more than a month.
The upside of contacts, though, is that I actually do see better with contacts than glasses. I think it's because the lense is actually on my eye rather than an inch away. It's a pretty noticable improvement when I switch back and forth.
If you have any more questions, feel free to ask.
If you're interested, I might even tell the story of how wearinbg contacts made the first time I was pulled over an experience I'd really like to forget....
