What does the cursor mean in iTunes when you hold Control?

Your guess is correct. That change in the cursor is a tiny little visual representation of the context menu.

Yes, it signals the secondary click coming up :)

Easier to get a two button mouse :)

Actually all MacBooks have secondary click on the trackpad. You just click with two fingers instead of one ;)

@btko
This gets brought up all the time. Not everyone agrees with you. Having two buttons on a laptop always gave me wrist problems. For that reason, I prefer control-clicking. Seriously, this isn’t even bringing up. It’s the oldest, most over-used complaint in the book.