Darvond: Do you prefer building things yourself, packages that might literally be years out of date because Debian so chooses, or up to date things?
A lot of out of date stuff will work fine 99% of the time. I remember upgrading from redhat 4 to say 4.6 or something, and a lot of it were utilities that although had some fixes didn't really affect the system as a whole. Not only that the
'improved' packages for XWindows, Gnome and
KDE slowed down my computer so much (
400Mhz I think) that I preferred to downgrade.
Stable versions unless it's something that has to be the latest and greatest will probably work fine. This is from my experience.
As for building things myself. No, there's often too many things I'm not sure what the packages are for, so I'd take the newest version unless it required some odd package nothing else needed. Best to go with some stock version of Debian or something with a good solid layout and stick with it.