Hello Michael,

You got it, "lazy" is the right word for that Align with Dimension behavior.

As far as where to align and position the arrowhead and measurement information on the dimension line that decision can be as variable as the individual as the part being modeled. In that case I'd think manual flip/toggle makes sense so as not to add complexity.

Nice to hear curved leaders are a consideration for the future, it just broadens MoIs technical illustration appeal.

The last few drawings on this page give an example of dimensions stacked from a datum:

https://ocw.mit.edu/courses/mechanical-engineering/2-007-design-and-manufacturing-i-spring-2009/related-resources/drawing_and_sketching/

Could the existing Align tool be extended to not only effect position but also distribution? For example, select multiple horizontal dimensions, Align > Distribute would provide for spacing between dimension lines in the selected group. Also, selecting multiple leaders Align > Distribute > Left could effectively box in the dimension data. This way you're using an existing tool that is familiar to the user and not adding complexity by adding a screen. The user is confident that what they are seeing on the screen exports as they see it.

On another dimension note do you see any potential risk for confusion by allowing the user to fix scale options in two places?

Thanks.