I knew someone who did this but swapped out the physical hard drive each time. I wouldn’t dual boot because then it’s much more obvious to IT what you’ve done.
This is only realistically feasible though if the hard drive is easily accessible. If it’s something like a Mac or soldered in dual booting is your only choice. As others have said, this could get you in a lot of trouble with your company. Check the docs you’ve signed
You having regrets depends on your expectations. If you want a very stable system with little maintenance then you’ll be happy. Packages will be older but that’s what makes it easy to keep stable.
I’m not personally a fan of vanilla Debian because the stable versions are a bit too outdated for the things I like to work with. I do use Debian derivatives though the LTS versions.