Why file all the time ?
To answer the original post: I take my chains down to the witness mark, if the chain lasts that long. Every part of a chain can wear out, and if any are worn out or damaged beyond repair, pitch it.
Regarding the issue of how far to sharpen the teeth: it's ok to take the teeth back to the witness mark, but I haven't heard anyone mention taking down the depth gauges. The shorter the length of the tooth (not the height!), then it becomes more important to increase the cut depth by adjusting the depth gauges. On a relatively new chain, I like 30 thousandths clearance. Aggressive cut, tolerates a little more wear before it starts making sawdust instead of chips. As the tooth gets closer to the witness mark, there is a greater tendency for the chain to rock backwards from the proper cutting angle, and I increase the grind on the depth gauges to 35-40 thousandths clearance to compensate. Lower the depth gauge to much, especially on hard wood or with a weak saw, and you have made the chain impractical to use.
For all you dedicated hand filers: Do you take a brand new chain and hand file it before you use it? You don't think that Stihl has an army of mountain gnomes hand filing all their new chains do you? They come from the factory sharpened by a grinder.
The old argument about how hand filing is better than machine grinding is not true. It is true that bad grinding is worse than bad hand filing. It's easier to damage a chain with a grinder, because it has more horsepower and goes a lot faster.
Just like hand filing, sharpening with a machine made to do the job takes a bit of training. If the operator doesn't know what he is doing, or doesn't care, then the result will be poor sharpening or damaged chains.
My humble opinion on the whole topic is this: hand file when you are in the field, and don't have a replacement chain or mobile grinder. Small chains or chains that are only a little dull can often be hand filed quicker than you can dismount the chain. If it's quicker, hand file it. It's all about money, and time is money. I can bench grind a dull 20" chain MUCH faster than anyone can hand file to equal sharpness. I can have a stack of chains sharpened faster than most people can drive to a dealer twice to deliver and then pick up chains.
If anybody wants to learn how to use a bench grinder, there are lots of places to learn. If you use chainsaws for a living, you will save money. A tree service not owning a chain grinder is about as silly as a tire repair shop not having a tire machine. Sure, you can get by without it, but why ?
Spend the extra $200 for the BOROZON wheel (some people think they are diamond wheels, but they are not). They cut the steel, rather than abrading it. Almost no heat involved, and the filings don't even burn up. It is actually difficult to burn a chain tooth with that wheel, which can still be hand filed because it was never burned by the bench grinder.