Sorry, I missed this comment. I actually love doing that kind of shit, I get some sort of weird pleasure out of fixing chaotic stuff like that. That tends to be my role almost all the time; I'll come in, stay a few years, fix everything and get bored, and then move on somewhere else to do it again.
My current job is the only place that I haven't done that, because it's probably the best company that I've ever worked for.
My condolences. And as much as I hate Posit/Workbench, some of that is on your IT department. If I'm reading your comment correctly, you're having issues because it needs admin privileges to update some things, namely packages. That's honestly a very simple fix, they just need to grant your user NTFS write permissions to the Rstudio/Workbench install directory locally (and maybe some registry keys, but that's not definite). That's it. It's a 10-second permanent fix and no more UAC prompts for you.