Please remember that Debian comes in Stable, Testing and Unstable flavours. Frankly I have fewer problems with Unstable than I used to have with any version of Windows.
There is also "Experimental" but i would recommend safety clothing before playing with it :-)
The way Debian works, Unstable is cutting edge (for Debian anyway). Packages then drift down to Testing and finally to Stable. With Unstable you always have the latest and greatest - at a slight risk of course. Version numbers are irrelevant here. I installed debian once, over six years ago, and have had a relatively pain-free (almost boring) experience ever since.
Interestingly, I twice unsuccessfully tried to install Ubuntu on clean machines - Crap! Now I won't touch it - it has gone "commercial"