Ken is Absolutely Correct.
Don't give your Pumpkin The Shaft ! - LOL
The only part of the bit that cuts is the Flutes, If the bit is too deep into the pumpkin, you are tearing through the foam with the Shaft.
This is why the paint ripples up. (that's like carving a Turkey with a butter knife)
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Now as far as the TWO Pass, What this really implies is to Outline the Design First ! I now use a 1/64" Drill bit for this, But a 1/32" will work just as fine.
You just want a little of the bit outside the Chuck, and go around the shapes. Just deep enough where you see some dust coming up.
With these outlines around the shapes, you are also placing a track (or Gully) around the shape, so slip offs, off the shapes don't happen as much.
Some Folks do the outlining with an X-acto knife, it will give great results, but I just don't have the time to do it that way.
On the Below Image:
The Solid Black is the Chuck/Dremil - Just have enough of the bit out to go into the foam about 1/16" of an inch. With a little Bit Left over for space between the pumpkin and the dremel chuck.
The Outlline BOX = the amount of bit that goes in the pumpkin.
if you haven't already - take a look at my tutorial - I not only show the process in step by Step with photo's,
But I also list all the bits I use. for each Step of the carving process.
http://www.stoneykins.com/Forum/viewtop ... f=9&t=2308
I got one foot in the grave the other on a banana peel !
The Pumpkin Carving Group - Facebook Group