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My Oregon raker files seem ok. I've been using them a good bit, mostly on Stihl chain, and they continue to cut well. I got two sets. They came with a file and a gauge for about $7 each.

Files are like lighters and magic markers. There's always 'one more use' you can get out them with sufficient effort. After it starts taking force to file a chain, I semi retire a file. I save a couple for hacking on trash chains, or filing non saw stuff, but I like a nice cutting file.

I figure 3 files per chain. I get a bit more out of them, but that's a good figure. Buying by the box, that adds about $5 to chain cost, so $n for the chain + $5 to keep it sharp.

You don't like Stihl files? Those are my favorites, but Pferd is acceptable also.

What do y'all think about sharpening on the spot? Would that please you, or piss you off? If I dull a saw, I plant my ass on the ground and sharpen it, but it isn't my occupation, and I don't have time constraints.

So, how's that work in practice? You got a guy in the tree, a guy on the ground breaking stuff down... Guy on the ground hits some dirt or a rock, and... Everyone stands there looking at each other?

More than climbers imo. Once you graduate from 'occasional homeowner use', you should know how to maintain your tools. Doesn't have to be perfect, but you should be at least good enough to get work done.