There are 2 cutting edges on each tooth / cutter: one on the top plate, and one on the side plate. Both edges have to be sharp.
But the 'full chisel' chain that you are using also has a point or 'corner' that leads it into the wood. This point can get ground / abraded away (like yours), or bent, in which case it actually pushes the cutter AWAY from the wood. Does not matter how sharp the other edges are, or what your depth gauges ('rakers') look like if the corner is damaged like that. @Del_ got it right in his post:
Typically, it is easiest to remove that much metal with a chain grinder. It also lets you 'even up' the cutters and start fresh. Maybe pay someone or a shop $7 (or whatever) to save a $20 chain, even if it is just to learn from this, and to practice your filing. Hold it up next to a new chain to see the difference.
All that other stuff matters, but does not seem to be the key issue with the chain in the original photos.
Philbert
But the 'full chisel' chain that you are using also has a point or 'corner' that leads it into the wood. This point can get ground / abraded away (like yours), or bent, in which case it actually pushes the cutter AWAY from the wood. Does not matter how sharp the other edges are, or what your depth gauges ('rakers') look like if the corner is damaged like that. @Del_ got it right in his post:
See the small white arrow I added? That is about how far you have to go back to get to where metal from the tooth is whole.
Typically, it is easiest to remove that much metal with a chain grinder. It also lets you 'even up' the cutters and start fresh. Maybe pay someone or a shop $7 (or whatever) to save a $20 chain, even if it is just to learn from this, and to practice your filing. Hold it up next to a new chain to see the difference.
All that other stuff matters, but does not seem to be the key issue with the chain in the original photos.
Philbert