I've never met anyone who got rid of any classic video game stuff who didn't regret it. The moral of the story is, don't. This is why I have an entertainment center full of stupid old consoles and three bookshelves full of games for all kinds of systems.

A few systems I traded in over the years to fund newer consoles when I was young and didn't know any better. I got all of them back, though, and in most cases before they became trendy enough again for the used prices to skyrocket.