Have a View Independent 180 text option. This will allow a text element to be placed at a desired angle, and only rotate by 180° if view rotation puts text at more than a 90° viewing angle on a sheet in a rotate view. This would maintain text readability per normal drafting standards but retain orientation relative to its placement but avoids showing upside down if the view is rotated.

Same comment made in ORD, where this would be highly desired:

Stationing Text "View Readable" Setting to Honor Rotated Views