I would have inferred he's talking about the complete OS, not just the kernel. In many cases, building the vanilla kernel isn't the best idea anyhow. Building from the vendor's source is preferred.
Anyhow, if you're referring to upgrading the entire OS, my experience with this procedure has been pretty good for both Red Hat Linux and SuSE Linux. The only caveat is that you might prefer to do a clean install for major changes.
I.e. I would upgrade Red Hat Linux from 7.0 to 7.3. But 6.2 to 7.3 is riskier, and I would prefer a clean install.
SuSE versions their product differently, so for current releases, it's relatively safe to go from SuSE 7.1 (or later) to 8.0.
In general, upgrading Linux OS distributions works better than upgrading Winblows. In theory, you can start from versions older than I've recommended, but again there would be higher risk of breakage.