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 uplo
Yes you should generate a new ssh key for every workstation. Also make sure to specify a passphrase for your private key and keep it safe. Never share it.
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