I have been having so many problems with Illustrator lately and just now realized that it is because of my UltraWide monitor and the fact that I have Windows Magnification set to 200%.

This is not being handled well in Illustrator. It's making the active area around a selected item way too big. I can be 100px off of the selected item and it still wants to rotate. I try to select a point and it's nearly impossible. If you look at all of the "tolerance" bug reports, I would be willing to bet they all deal with magnification levels above 100% that Illustrator isn't compensating for.

To test it, I changed my magnification level to 100% and suddenly, the rotate tool disappears when I am just a little bit off of the selected shape like it's supposed to. Somehow, the tolerance distance for things like rotate or transform or selecting handles is way off when Windows desktop magnification is greater than 100%.

FIx this problem and you can literally close a dozen or more trouble tickets.