Something I have not seen in any post above is the size of your saw chain, make of chain and bar length.
Everyone has their favourite and I do not want to get into a brand war. I have 4 saws, 2 Husqvarna’s with 20 inch bars, and 2 Stihl’s, both with 16 inch bars. I have used .058 and also .050 chain on the Huskies, both are great but I have the best luck with Stihl chain, it just lasts longer from my experience.
I have an Oregon electric hand held sharpener same/similar as shown in other picture's in these posts. I also have a complicated jig that uses a file but seems to take a long time to set up and move. The hand file, with a guide is my most common sharpening tool and pretty hard to beat plus it can be used it the bush without any problems.
As soon as the saw starts making sawdust instead of chips I know it’s time to sharpen as cutting just takes too long. The saw should not require any pressure to cut, if you have to force it too work then it’s too dull, the chips, sawdust are your guide as to what’s going on.
I also agree with taking the chain off as you need to tune the bar up, clean the groove, check the nose sprocket if it has one, remove (file off) any raised spots on the bar and try and keep everything in a free turning assembly. Flipping the bar allows you to create even wear on both sides of the bar. With the bar off it’s a great time to check sprocket wear, clean your brake, and also to grease you clutch bearing, often overlooked until it fails and ruins your saw.
With the bar off it’s also a good idea to insure your oil supply holes to the bar are clean and no better time to clean the chain as well.
My best friend for servicing and maintaining my saw is compressed air, nothing is better in having a clean saw so you can inspect all the different saw components and keep the air filter area clean.
All my saws have there own case and they live in the cases, keeping the saw out of the dirt start with storage, I have a rag in the bottom of all cases, as guaranteed the bar oiler is going to leak.
When not using your saw for extended periods, empty the oil and fuel tanks so they remain clean and prevent leaks, stale fuel is no one’s friend.
Only use your saw when you are clear headed and rested, not doing so is just a recipe for disaster. Chain saws are not nice to you if you do not respect them, where you hearing protection, eye protection, hand protection and leg protection. Just purchased a pair of bucking pants, not chaps as I want full, leg protection, May be too warm but the protection is worth the trouble.
I use my saws for fire wood and property maintenance, burn about 6-8 cords a year and have close to 300 acres of bush to keep me busy.
For the senior group, I am 72, have a look at the Stihl Multistart saws and tools, nice for those older senior arms and bodies, in my opinion.
cheers.