Pyro,
That is how I've always cut wood. Typically after the tree comes down and the limbs have been cut down to firewood size and removed I'll try to drag the trunk to where ever it is I'll be splitting the rounds that are about to be cut from it. Then I'll cut through the tree at intervals as deep as I can make the cut without the kerf closing and trapping the saw. They get stuck sometimes. That's why I carry a spare bar and several sharp chains with me. If one gets stuck you just unbolt the guide bar, take it off the saw, put the spare bar and new chain on the saw and then move on. If I find a place where a natural crook allows me to cut the trunk all the way through all the better. I like to get it to lengths that I can roll over without killing myself. Anyway 2/3 on one side and 1/3 on the back side is about how it works out. I will use any surface on the guide bar I can get into wood - top, bottom, tip, it doesn't matter to me. As I said, we take spare chains into the wood with us. I resharpen all the chains at the end of each day.
As for your chain sharpening policy I simply can not support it. It is not beyond any man to learn how to hold a file in his hand and make straight and consistant strokes in one direction. There are aids to hold the right angle and depth. The only trick to it is buying a vice to hold the saw and then be willing to practice for about one good afternoon. Baring that locally they get $7 to do a chain off the saw and $13 on it; you can buy Stihl chains all day long on E-Bay for less than $20 so its up to you which way you want to spend your money.
That is how I've always cut wood. Typically after the tree comes down and the limbs have been cut down to firewood size and removed I'll try to drag the trunk to where ever it is I'll be splitting the rounds that are about to be cut from it. Then I'll cut through the tree at intervals as deep as I can make the cut without the kerf closing and trapping the saw. They get stuck sometimes. That's why I carry a spare bar and several sharp chains with me. If one gets stuck you just unbolt the guide bar, take it off the saw, put the spare bar and new chain on the saw and then move on. If I find a place where a natural crook allows me to cut the trunk all the way through all the better. I like to get it to lengths that I can roll over without killing myself. Anyway 2/3 on one side and 1/3 on the back side is about how it works out. I will use any surface on the guide bar I can get into wood - top, bottom, tip, it doesn't matter to me. As I said, we take spare chains into the wood with us. I resharpen all the chains at the end of each day.
As for your chain sharpening policy I simply can not support it. It is not beyond any man to learn how to hold a file in his hand and make straight and consistant strokes in one direction. There are aids to hold the right angle and depth. The only trick to it is buying a vice to hold the saw and then be willing to practice for about one good afternoon. Baring that locally they get $7 to do a chain off the saw and $13 on it; you can buy Stihl chains all day long on E-Bay for less than $20 so its up to you which way you want to spend your money.