I dunno why you think this is a "crappy thing", given that it's never worked before. (For some definition of work, that is. In any case, it certainly does't work *less* than it did before.)
I used up2date tricks to go from RH8 to RH9 (replaced redhat-release, ran up2date, boom upgraded) and from RH9 to FC1 simply by downloading the apt-get FC1 RPM from fedora.us, installying it, and apt-get update && apt-get dist-upgrade.
I'm not running anything crazy (UML/SELinux/not even X), it's just a small server for friends and family. I'd assumed by how well it worked in the past that it was supported (I'd read about the procedure on a forum). Was what I did before no more dangerous than doing so now? The biggest change I'd have to worry about if doing it "by hand" would be the upgrade to 2.6 I'd guess.
Anyway, I wouldn't want to be stuck in this situation with *any* distribution.
It's a small server for friends and family. If it were anything serious I'd be on RHEL in a "proper" COLO anyways :) I just know i'm not the only one in this situation, as these cheap dedicated providers have been springing up everywhere!
