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People that hand file don't typically swap out chains and save the used ones to file later. If it can be filed, it gets filed then and there. Otherwise it goes in the trash. People that swap out their chains typically have a grinder to sharpen them.

I tried using a file guide once, didn't like it. Once in a while I'll spot inconsistencies (filing too high or too low) and compensate to correct it. But for the most part I can use the chain until it's used up without losing cutting efficiency.

I prefer advancing the chain for each tooth, keeping my filing position exactly the same for each tooth in order to retain consistency. My body, hands, file and chain tooth are all in the exact same position so it's simple muscle memory and every tooth is treated the same. This makes it so I...

My truck is a bucket truck. It's under the tree being worked on.

Fortunately my truck is always right in the middle of the work site. ;) My knees don't let me file a saw on the ground any more.

I mounted a vise on the bucket truck just for filing. I'd post a picture but I cannot access my photobucket account right now.

I file loose chain all the time, I just press the side of my index finger against the side of the tooth as I file with the other hand. Done it that way for years, works fine as long as the chain isn't sloppy loose.