... Serenity -
Debian GNU/Linux 7.5 (wheezy) ...
Long story short... If I was gonna do this upgrade at all, I had to do it now or forget about it altogether. Well, forgetting about (not maintaining) a machine I need is simply not an option.
It turns out that this upgrade was simple and straightforward. I suppose my one year delay in doing it was one of those life things, but it's been on my list for a year now. So, it was time to jump.
Honestly, most of my delay was due to painful memories of upgrading from Lenny to Squeeze. That life stuff, you know. The final nudge making me jump to Wheezy was the simple fact that sooner or later (sooner in this case)...
"The Debian project is pleased to announce that although regular security support for Debian GNU/Linux 6.0 (code name squeeze) will be terminated on 31 May, long term support for the distribution is going to be extended until February 2016, i.e. five years after the initial release." (source)
So, if not now... When!?. Wheezy is working very well for me after a quick and smooth upgrade. Of any of the "official" Linux distros out there, Debian is still the best one for my needs. Give it a go if you like.