After a year or so of sporadic attempts to properly sharpen my chain, I've isolated the issue. It all came down to one simple mistake I was making. Prior to discovering this mistake, I tried sharpening with a dremel+chainsaw bit, got it sharp to the touch, but it wouldn't cut correctly. I then bought a manual file and got it sharp to the touch, but it still wouldn't cut right. I then tried filing down the rakers, but that didn't help either. I finally figured out what it was. When I first attempted to sharpen my chain a year ago, I had read some place that you're supposed to hold the file at a bit of an upwards angle when you sharpen, so I've been doing just that. Tonight I looked at the cutters under good lighting and realized the top of the cutters weren't getting sharp. Evidently, I've been holding it at too much of an angle, preventing the file from making contact with a good portion of the top of the cutters. I straightened out my file just a little bit to match the natural angle on the cutter, ran the file over each cutter a few times, and voila, it cut like a new chain. Big chips were flying out all over the place. My saw was once again having a hard time keeping up with the chain, not vice versa.