I started way back with a copy of Redhat either 3 or 4, that a friend of mine who was a fellow RPG 'er at the time. I liked it so much that I ended up buying in a box 5, then pre-ordering 6.0. I left then as rutienely going through and upgrade hell, I spent most of the time fixing and finding work arounds than actualy getting anything done. The Box set of Redhat 6.0 is sitting behind me still.
Later on tried Slackware in 110 floppies to get it on a 486 xp laptop (Microcenter branded laptop not to be confused with Windows XP). It was a resurecturion deal, found out the next version HAD working vid configurations after learning to build my own vid card driver.
Went with Fedora 1 when the change over happen, and I would dabble in it for a while but was primarily a Microserf, certified in it for employment. (no companies localy used linux, so only jobs where MS ones)
I would torment my self with fedora, or slack or various others until about three years ago I found Ubuntu and for once, EVERYTHING worked out of the box with no tweaking and work around for me. I used the Wubi for about two months to make sure I just wasnt into upgrade hell, or to find out the catches.
My time in linux actualy earned me a System Admin job, when I found out they where useing SCO Unix, and found out why no one else took the job... the hard way.
Since then, Ive tried arch, didnt like it, repos where hit or miss for me. Tried fedora that upgrade hell hadnt changed but Ubuntu kept it simple but still let me do customizations (very big thing for me), and just recently made the switch to Kubuntu. I didnt like 'web aps' didnt like the 'online searching via dash' and the extra weight for thoes I didnt like either, and you had to bend over backwords to customize the scree. Under neath Unity, I got no complatints, and 2 years ago, only one VM has MS for ham radio programing, but other than that there are no microsoft computers here any more. But I still keep up in the MS world, as thats where the work is here. Hopefuly some day soon that will change