So yea, how 'bout them CAD packages....
I have no experience with Pro/E, but from what I've seen Solidworks is pretty straight forward on accessing the various objects and symbols and being able to apply them in the manner needed. I don't think I've ever come across any issues with graphical errors, or an inability to attach things as needed. For example, there's issues with some softwhere, where a Datum attach to a circle will not appear "just right" because the trianglular leader-end / arrow will not conform to the curve of the circle. You end up with a triangle on the end of the leader with a tangent flat-side, rather than fully conforming to the curve, and it looks weird.
I find NX is a bit too 'picky' about how to attach/place GD&T frames extended from a surface - these are things that make software easier/harder to 'use' GD&T in the drawing end of things. I would barely consider the differences as having any amount of weight in software decision-making, however. They are all "good enough" to get by with, and any minor issues like I mention are made insignificant by the pros/cons with the general modeling, file management, and whether or not the software is best for "the type of work" you do.