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Presumably, you won't be working in there when it is -5C, so can't you just take a laptop PC into the shed when you go there to work? It solves any potential physical-security problems too. You ...
dd and dd_rescue. See also, this question: Using DD for disk cloning
Don't try to fix anything yet. Make sure you know exactly what the real, underlying, problem is. Now starting fixing things. If there are multiple things to fix, carefully consider which things can ...
See also: What’s your checklist for when everything blows up?
On *nix systems, I usually use Dia, despite its warts and ugliness. On Windows, Inkscape is a really good choice. An Open Source vector graphics editor, with capabilities similar to Illustrator, ...
Day-to-day, I think it makes very little difference. In fact your organisation might benefit more from the free alternatives, with their typically more up-to-date packages and vibrant community ...
Do you really need the password? A possible alternative would be: Add a new disk. Reinstall the OS. Access data from the old disk. (If you do need the password, I recommend ntpasswd)