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In my experience, the easiest way is to use a software for central management of signatures, such as Set-OutlookSignatures. Set-OutlookSignatures not only allows you to use Word or HTML templates, it also includes features to ensure maximum signature compatibility across different mail clients. There is also a lot of other features that come in handy, such as support for roaming signatures.
For designing signatures outside Exchange/Outlook, I would stick to the great compatibility overview provided by Campaign Monitor, and additionaly use tools such as PreMailer.