I started with Debian on CDs, but used Gentoo for years after that. Eventually I admitted that just Ubuntu suited my needs and used up less time keeping it up to date. I do sometimes still pull in a package that brings a million dependencies for stuff I don't want and miss USE flags, though.

I'd agree that the manual Gentoo install process, and those tinkering years in general, gave me experience and familiarity that's come in handy plenty of times when dealing with other distros, troubleshooting, working on servers, and so on.