Yes, many and those are really hard to get around. Two views at the same time eliminate the vast majority though so that's why the system now works that way. A third view would likely get rid of the remainder but is for various reasons very hard to implement reliably.

Yes. Imagine looking at a 2x2 brick [0] and a 2x4 brick [1] head on.

[0] https://brickset.com/parts/design-3003

[1] https://brickset.com/parts/design-3001