I've been using the Spyderco Sharpmaker (and now the Gauntlet) as well as the Lansky V sharpeners for the last 15 or so years.
Suggestions:
-Use the 'countdown method' to sharpen.
5 passes on left side of blade, followed by 5 on the right side.
4 passes left, 4 passes right
....
1 pass left, 1 pass right
I found this more reliably produces a razor sharp edge then the factory suggested alternating 1:1 pass method.
For a new knife, I start at 10 strokes for the countdown to get the edge accustomed to the angle (20 degree) of the sharpener.
For subsequent maintainence, I start the countdown at 3-5. Thats usually plenty to restore a 'sharpish' - cuting paper, but roughly - edge to shaving sharp.
- I would not suggest over sharpening.
I use a simple test for when to sharpen, called 'the plastic test.'
A sharp knife should be able to cleanly cut the plastic film on a tissue box / case of water by simply dragging the tip across the plastic, using only the weight of the blade.
Once its no longer able to do that, I do a touch up. Typically for me thats around 1x a month.