I have used illustrator for over 20 years. I am about to go crazy. What's with them changing it or doing something so it's hard to rotate, scale or move objeccts. I used to hover outside of an object and I could see the rotate. Now it's hit or miss. It takes multiple tries do do what I want if I want to rotate, scale or move.
I feel your pain! I've noticed things like this too, that seem to pop up in different versions of Illustrator. The Selection tool makes you hover really close to the object to get it the rotate cursor to pop up, which can be frustrating.
I have one tip/workaroud for rotating when the rotate cursor is being fussy, I use the Free Transform tool shortcut E, this gives you a rotate cursor that you can use no matter how far away you are from the object. I've been doing it for so long it's now second nature to just hit the E key, rotate, then go back to the Selection tool.