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This is a newbie question from a Windows guy but when I work with Git or other software relying on (Open)SSH, should I generate a new SSH key for every workstation and then upload the public key to GitHub / BitBucket etc. or should I be reusing some previously generated one? Or does it matter at all?
You should generate a pair of keys for each workstation. This way, if a key is compromised you will be able to revoke permission for that key only, without affecting other workstations