I'm guessing that you want that swoopy curve at the top of your plunge lines? Hanging the belt off is the way to go but it takes a steady hand to get both sides the same. And as Ken mentioned, it's the j-flex belts that really give you want you want, but you still want to hang your lower grit belts off too so that you don't get a hard, deep plunge cut with those deep scratches that nobody can ever get out. You mentioned that you're using a file guide to grind. That's a great method. A good trick to use with that is to do all of your bevel grinding up through 120, then sneak your file guide back 1/16 or so. Your 220 j-weight belt will then remove all of the previous scratches in the plunges and make a really pretty plunge line with that swoop at the top you're looking for.
You can angle your blade to increase the arc length of the swoop. A tiny bit of angle goes a long way.