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I'll bet there are very different answers depending upon one's personal experience and preference.

I find in both Chinese vegetable-type cleavers and Western Chef knives to have a strong avoidance of dead-flat blades. I find them to cause just as many cutting problems, like "accordion-ing" and other incomplete cuts, and forces me to focus more on making sure the knife falls fully flat on the cutting board. Too much thinking for the task at hand. :) In general I prefer some amount of belly to a blade - ranging from slight belly (French profile chef knife) to what is called around here "excessive belly" (German profile chef knife). My cutting technique tends to have a bit of a rock and roll to it rather than being stiff-wristed.

For paring knives, however, I've done what you are thinking about and ground out the belly to make them dead flat. Better for cutting-in-the-hand in my experience.

So to answer your questions:
1. I think (my opinion) it may be your technique. I don't think a flat blade is necessary or desirable (my opinion) to get good clean cuts. There are other factors to consider, though, that affect the cutting geometry -- ergonomics, such as how you are holding the knife, how tall you are, how high the counter is (including the cutting board) and that relationship.
2. Not sure what "blade geometry" would get destroyed if you also do the proper thinning when you put the new edge on it... but I'm sure others may have more to say on that. I stay away from power tools when doing anything with the knife cutting edge. A coarse stone will do the job quickly enough. Metal files... put them back in the toolbox. :)

In general I don't think your approaching from the wrong angle. But consider some of the other factors first and then do what you need to do. The Winco would be the perfect candidate to flatten and see if that solves your dilemma.
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