I'd really like to get a Debian system up and running, and I've tried many times in VirtualBox to see how I get on. Trouble is, and I hope I'm not alone here, I like to run things that are stable and released, unless I specifically want to test new software that is still in alpha or beta. So the way I see it:

Ubuntu 8.04 is equivalent to Debian 4.0 stable, since they are both stable, official releases.

Ubuntu 8.10 beta is equivalent to Debian testing, since they are both somewhat tested versions of the next release.

Ubuntu 8.10 nightly builds or something is the equivalent to Debian unstable, since they both have mostly untested packages.

(I know Debian has an even more bleeding edge level of experimental, but I won't even go there )

So I want to install Debian stable, which works beautifully and is rock solid, but has the outdated packages problem. Updating to testing from stable is meant to be easy, but I have done it several times and it will not boot from the new kernel that gets installed, only the old one.

Installing Debian testing directly works fine, but something irks me about using that as my desktop operating system. I want a nice released final version, the equivalent of what Ubuntu delivers every 6 months.

So, is it better to stick with a distribution like Ubuntu, intended to deliver Debian in a more up-to-date way? Should I just go for it with the Debian testing ISO? Is Debian stable enough? I'd still love to know where I'm going wrong when I update stable, unless maybe it is VirtualBox related?

I know this is kind of a pointless post, but I've always thought it would be nice to run Ubuntu's base, but never really been able to get my head around the best way to do it. I'd be interested to hear other people's thoughts and what they think of the versions of Debian.