I really like doing stippling, I find it really relaxing. To me, there are several things that make it go easier and look better.
(1) Correct speed - If you have the speed to high then you are "rushed" in trying to keep up mentally with the machine. If too slow, then the stippling will look jerky. Figuring out the right speed for you takes some time to get in the right "groove" with it.
(2) Looking ahead - As I'm stippling, I'm looking ahead to where I'm going rather than constantly watching the needle. This is a constant back and forth mental thing but it helps me not end up with myself painted into a corner.
(3) Develop a pattern - I try to keep the pattern curving and not allow myself to get into a squiggling line instead.
Below is a pic of wall hanging I did that had a lot of stippling in it. You can vary the pattern of stippling as well, so instead of doing a tight meandering stippling like I did in the background, for the inner circle I did a looping stippling. Lots of fun! :)