Chris, I would suggest getting slink up and running first. Then you can upgrade away to your heart's content. I too tend to get into the upgrade habit. Interesting that sometimes that becomes the end in itself really... :-)
On slink, I have had things work under debian that should have worked under other distributions but didn't - particularly kernel/lib related stuff and package setups. I am very impressed with the stability and robustness of the dist and the deb/apt system. It also gives a complete ability to upgrade any or all packages. Good luck. Regards, Jason.