The problem I personally have had here is that Debian support cycles are way too short, 1 year past the bi-annual release of the new version. Even the squeeze

The problem I personally have had here is that Debian support cycles are way too short, 1 year past the bi-annual release of the new version. Even the squeeze LTS 1 year additional support experiment is too short. Hence my new appreciation of RHEL. With Windows there's a very good chance you can continue using an old version for a long time. I'm still supporting my mother using XP through two sets of hardware (although that'll end soon). (In)Famously, many people skipped Vista and are now skipping Widows 8, and I gather not suffering all that much.