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My first Linux installation was RedHat, back in 2002, because many people and companies used it. So I decided to learn from what was the most popular. Then within a year or so, I switched to Mandrake as I was told that it was more user friendly compared to RedHat. After a few months, I found that Slackware maybe the one I was looking for because I was really sick of the RPM dependencies and I was quite happy with it. Several years later, my colleagues persuaded me that Debian is easier to maintain because of its package management system so I gave it a go. However, I switched back to Slackware a few months later eventually.
People might ask why I dumped a supposedly easier-to-maintain distro in favor of a nearly-plain-vanilla Linux distro. As a developer, I think I have the need to figure out what (libraries / programs) go together and what don't myself. If I "outsourced" the maintenance to a package management system, I may never realize all the gotcha's and hence losing the opportunities to know, which is not good to a professional.