@DSurman Thank you for the additional context, I can feel your frustration and understand that it’s not ideal to have to modify the fonts every time.
Outlook is always going to be an outlier in terms of fonts and styles in email, it is one of the most restrictive as far as CSS is concerned.
I think your “paste and match formatting” idea is great, you should add it as an idea here - if you share the link back in this thread, I’d be happy to upvote!