Late to the party, but what the heck. I used to carry a bunch of chains, like five or six for a days cutting.
My mantra is safety in the woods. Everytime the saw needs gas, the saw also better need bar oil, and if I am properly hydrated I should need to pee. This is (was) a great time to walk back to the truck for another bottle of gatorade, and the tool box with all the chains in it is more likely to make it home if I leave it in the truck.
So it used to be I would come home from a long day of cutting, exhausted, and have five or six chains to sharpen, after I unloaded all the wood I had cut. Sucked.
I set a goal to be able to field sharpen a chain as fast as or faster than I could field replace a chain. I had a few cords go by under the saw before I got there, but with a couple seasons of working for it, I can now touch up a chain in the field with a file faster than I can change one. I still carry a spare or two, but not five.
The main struggle for me was getting the teeth facing opposite ways equally sharp. If you are cutting a round off a log and the cut wants to go to the left (your left, as you watch the bar dropping through the log in front of you, well, you too are a right handed sharpener and the easy teeth to sharpen are sharper than the hard ones to get at.
I tried a few different ways, what ended up working for me was to go around the chain once, sharpening all the teeth as i go - but spinning the saw back and forth on the tailgate of my truck like some kind of maniac. One tooth, spin the saw, one tooth, spin the saw, one tooth, spin the saw - advance the chain- one tooth, spin the saw, one tooth, spin the saw and etcetera.
I generally sharpen after every two tanks of saw gas.
I do use a file guide, and a speed handle on the file. Both of them together were under twenty bucks.
I only fool with the rakers after 3-5 teeth sharpenings. When I know the teeth are sharp but the chips are small, rakers.
FWIW I do sharpen a factory new chain before I start cutting with it, and resharpen when it gets to be about as dull as a factory new chain.
Are all y'all lubing the teeth with bar oil before you take a file to them? I got one of those old time metal cans with a gooseneck nozzle and the clicky-clacky feature on the bottom metal panel, like engineers on steam locomotives used to use, only smaller. Holds maybe half a pint of so. I find it quicker to file lubed teeth, and the file cleans up better too. The oil can was my grandpa's, I know he is happy that I am putting it to work.