Scott--
I have had a woodchuck for a year or so now. It is an awesome tool and Ken is very helpful. I just ordered his newest version last week. (for bowls)
I think there is a small learning curve. Keep the tool flat, and put some downward pressure on the tool rest. It will "catch" if you elevate either end. I also try to rotate/change the insert on a fairly regular basis. I maybe turn 20 pens per side. I buy the additional inserts from Ken and they are only $5.00 each. I throw mine away because I think they are inexpensive compared to all the other supplies we use, but many people use a diamond file to sharpen the back side of the insert.
If you watch some of the other you tube videos using the woodchuck, you will note that the turner is quite aggressive with the cut. IMHO, I would work my way up to being aggressive with practice of that tool.
Good Luck---pretty soon you will begin to feel guilty that you do not use your other tools much!