However, Windows is not my day-job OS, and I need to be economical with the time, energy, and number of neurons I spend babysitting that OS.
So what were you doing up until now? Reading each KB article? Vetting each update on a test system? I dont' really see that based on you response, so how on earth does THIS cumulative update model really change anything for YOU exactly?!!
Meanwhile, a dead simple off-the-shelf backup software packages for windows suitable for a single system seems like a perfect solution...
For example...this is pretty much exactly what you seem to need...but choose any you like.
Full Disk-Image Backup
Back up your entire computer including your operating system, applications and data, not just files and folders to an external hard drive or NAS.
You've already got the photographs properly protected; so this would be a perfect solution for the operating system.
that more likely I am to just switch to a platform that's more reliable and is easier to rebuild.
For Photoshop and Lightroom? What platform OSX? Here, I'll save you some time:
I installed the latest version of Mavericks and it broke some stuff (instruments) which I cannot afford to have broken. Is there a way to roll back to my previous release? Am currently on 10.9.2 and want to go to 10.9.1 or 10.9.
there is not an uninstall feature for patches, upgrades and even apps.
Unfortunately the only real way to do this is to wipe the drive, install the pervisous version, assuming you have the installer or can find it and restore from backup.
OS X invented cumulative software updates that can't be rolled back.
And Linux or BSD don't even run photoshop or lightroom.
So, what exactly is your plan?