Hello Kilroy and welcome to VSIDO..
What RatMan said..

I would also advise you to get to know and use fsarchiver.. it is by far the easiest and most practical disaster recovery tool ever.. EVER!
I have a How To on this forum to use fsarchiver It is a life saver.. As the developer I have fallen into some of the traps PackRat indicated.. They were both Perl related and it was I who didn't trust my gut and went ahead with the update.. Anyway, fsarchiver saved my ass because I had backups made and restored the developer / build partition in seconds.. that is NOT a misprint, in seconds I was back up and running .. also, SpaceFM (the greatest file manager ever and default for VSIDO) has builtin tools to backup and restore partitions with fsarchiver.. I SWEAR BY BOTH! Nad use both every single day
Another really good practice is to do a weekly dist-upgrade, that seems to be a good rhythm of updates without massive hits on your server (a lot of updates at once IMO is not a good thing so doing it weekly keeps it balanced)
Finally, do an fsarchiver backup before any major kernel updates.. this way if the kernel might not like you video card (rare now) you have the backup to fall back on...Just as PackRat indicated I try to remain at sid levels (dist-upgrade) every day so I see what is coming and I always make sure this forum is aware of it
This is something I wrote recently for twitter friends who did not know what VSIDO or SID was... It may also add some information to your decisions
When I created VSIDO it was a combination of what I knew and wanted and what several friends recommended and well the rest is history
I had been using Debian SID for several years and could not understand why it had such a bad reputation.. There were at the time a few SID distros but most have gone by the wayside..
I also wanted a distro that gave the newest user who downloaded it no more than 2 weeks of being a dist-upgrade of packages behind.. For the most part I have done just that.. Everytime there is a kernel upgrade or every 2 weeks I rebuild, test and deploy the distro.. It has worked out quite well
The other drive behind this was the frustrating world of Stable Debian where you have to wait 2-3 years for any new packages based on their release schedules..
Over the last 6 years of VSIDO and the 3 before it as I used Debian SID I can count on one hand anything that 'broke' my system because of a package.. Two of those three were because of Perl.. Classic case of the Perl devs not letting the application package maintainers the chance to catch up...
Other than those it has been an absolute joy
Mayhap more than you were expecting, but it is the story of VSIDO
Good luck and please don't hesitate to get in touch with any of us