When Windows 95 came out I was using OS/2 Warp. A friend of mine was operating a BBS and suggested I try this operating system called Linux. Going to bookstores I found some books that included some distribution or another, I tried Slackware 3.0.
The only challenge I faced at first was configuring X11 to work on my S3 Virge, once that was done and I could use more than the text console the flood gates were open and dove completely into this free 32-bit alternative.
It's been a very long painful road to take, but the joys of never getting a computer virus, or having a coherent system with files dating back to early 1990's far outweigh the pains of setting it all up. I use BSD for server duties, but I still use Linux to fix Windows machines and as a primary desktop. Compared to 10 years ago, Linux is dream to install, configure and use pretty much any distro.