Is there any way to flip the text and dimensions at the left so they don’t look upside down?
No, in common with other drawing software, the dimension orientation flips at 10 degrees left of vertical. yours is a little less than this, There is a Youtrack request to make the transition angle user selectable: https://mcneel.myjetbrains.com/youtrack/issue/RH-65027/Allow-Additional-Angle-Configuration-for-Keep-Text-Readable-Option. This is currently linked to a Rhino 9.x release.
For now, you could create a new annotation style to apply only to these pesky dims, setting the text horizontal:
Or flip the drawing objects so the slope is to the right instead of the left.
HTH
Jeremy
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