Like others said, chip size (relative to type of wood, hardness, frozen versus not, etc.) is a good way to test. However, simply looking at the chain is also a really good way to assess things, assuming you're running round-filed chisel chain and not semi-chisel.
When the leading tip of the cutter is not crisp and sharp, it's time to run a file over it. Peened and rounded out? It's gonna take a few passes with the file, at least!
The Stihl/Pferd combo sharpener tool thing works well. Not great, but well, and it is easy to use so you're more inclined to use it more often and not wait until the chain is dull. A swipe or two on each cutter is easy and fast to accomplish when you're topping off your tanks.
If you're cutting clean standing timber or tops that are still up in the air, you can go many tanks without needing a sharpening. Three or more is not unheard of. Cutting skidded wood or wood laying on the ground, I usually end up sharpening every tank full.
One other observation I made is that when I run a very short bar, I can get more tanks per sharpening because I'm not inadvertently sticking the tip of the bar into dirty things - the ground, the bark of an adjacent skidded log, etc.