Oooooooooooooooooooh I completely forgot about the bearing on it, very good point! The bit you linked is so cheap I'll buy that if I end up using the CNC rather than grinding down my old bit, thank you for your answers!

But hypothetically if the bit was $1000 or something, is it inherently dangerous to to use a bit with a bearing even if you lead in from the side and the bearing doesn't touch? Or does the danger come from cutting too far and damaging the bit or the CNC machine itself? I used to not worry about cutting too far and assumed everything would go as planned, but lately I've had bad luck and broke some bits (user error? machine error?) so I won't dare risk it with a bit this big.