Taemos is right. Getting games running in DOS was often truly painful. That kind of stuff tought a lot of kids about using computers and troubleshooting problems. Funny how people now have such a fear of typing in commands, especially when they're laid out so nicely on the web.
I once walked a guy through using XP's recovery console to repair a fried Windows install over the phone. He did quite well at it. When we were done I discovered he'd never used a computer before! Windows booted and he said "so what do I do now, click Start?" Turned out his kid was the computer user -- his curiosity fried Windows. That guy really had no problem just following some instructions on what to type in.
It's really just a question of taking the plunge. DOSbox is nice because it's pretty self contained. If you fry it you can just reinstall it. There's really no reason not to try and spend 30 minutes or so getting a game to work with it. I can't speak for front ends because I've never looked at them. At least with written instructions you also don't have to read them letter by letter too.