Thanks for the serious reply G4it.
Ok then. In all seriousness - U have 5 acres & time. So chainsaws.
Sharpen with a file in file guide just like every youtube vid ever says, level, appropriate angle, push not pull, etc. Additionally, use a small adjustable wrench or locked calipers as a tooth length gauge to ensure uniformity especially if you're having cutting issues. File rakers to specification after tooth sharpening. I prefer a straight edge laid across teeth on one side of the chain and a feeler gauge rather than feelers under a straight edge laid diagonal across. I don't like raker gauge/file guides. I like an aggressive cut so don't leave them high. I don't feeler gauge every time. Just ripping a little off with the file is ok if feelers previously established spec.
Remove the chain periodically and check that the bar isn't worn left/right unevenly so as to tip the chain. If it is make sure your oiler is a-ok, which you should be doing by proving a spray at start-up anyway. (Flip bar on reinstall to wear top/bottom evenly.) Stone/belt sand to square. Stone/file edge burr which you'll feel on the worn side. Bring your round file with you to the tree. And here's the magic info found nowhere on the internets, or in any literature, who the fuck knows why - if it pulls to one side through the cut, file the teeth on the opposite side. You don't just 'file the same number of strokes' as is universally, and incorrectly, advised. You make the teeth the same length as shown by your calipers. Then fine tune the cut by filing gently on the side opposite the direction it pulls.
Once you know that you file left if it cuts right, the condition of the chain won't get away from you to such a degree that you have to go to the calipers. So putting right a fucked chain needs the workshop - calipers, straight edges, feelers. But maintaining one that runs true just needs you to pay attention to which way the cut pulls, which makes sharpening quick, often a single stroke on one side only. No one tells you this.
This post is gold. There ya go. Don't cut your foot off.