I hear ya buddy. It's a PITA when it has to be done, but can be fun when it doesn't have to be and you're doing it "just coz".
A friend put me onto this web-service called Ninite (https://ninite.com/) that might help ease the pain. It's not quite the wonder-solution that the OP laments for, but it's a big step in the right direction.
What it does is present you with a list of popular applications from around the internet (eg Skype, WinRAR, Steam, etc), let you decide which ones you want (it offers choice, such as Firefox, Opera, Chrome), compiles a single-click application for you to download, and installs your extras for you. And know what's even better? It auto-denies any of the bloatware that ships with some products, such as Ask.com toolbar that comes with every bloody Java release these days.
such pain? i have alot of files from 2002 till today and i don't find them hard or anything. learn to get rid of files that you know will be irrelevant in the future or files that's too easy to get, i usually just keep most important ones then just sort them up.
I work on my computer and have no problem with it.
Reinstall Chrome, Firefox, Sublime Text, WinSCP and Adobe CS and I'm good
If you have a ton of work documents, back them up. It's not tough. Hell, most of us work on both a PC and a laptop so it makes sense to have it on an external anyway. Most things I work on are saved on cloud storage as well.