I have milled logs to make cabinets and furniture for 40 years with a sperber mill. ( chainsaw mill) I only sharpen chains with a pro electric sharpener. The sharpeners come in a million brand names and most of them look exactly alike. (which is weird to me) There's a lot of reasons to use an electric sharpener. They are accurate, and sharpen chains quickly. They are also expensive to buy, so unless you do a lot of cutting you can just do field "touch ups" with a file, and then drop them off for grinding at about $8. per loop at a sharpening shop usually, when they get bad or begin cutting crooked.
When you have an electric sharpener, you tend to do as Mr whoopee said, You sharpen all your chains before you go out to cut, and just change out the chain if your chips start to look like sawdust. Then when you get back to the shop, you sharpen all the chains that are dull and you are ready for the next cutting.
Old timers (I mean older than me by a few generations) got proficient at using files. They didn't need guides and could tell you what was wrong with your chain just by watching the chips fly.
It's worth understanding the mechanics of the way a chain cuts. Understanding that the rake height relationship to tooth height is important for pros, but maybe not so important to occasional users if it's "close enough". The same goes for tooth angles. somewhere between 30 and 35 works for crosscutting, but probably not important exactly what angle so long as they are the same for the right and left side teeth.
For most users, knowing everything isn't necessary, but knowing the basics is important.
Don't cut dirt or dirty logs whenever possible
When your chips start to look like saw dust, your chain is shot.
If your cut begins to curve then the teeth on one side have hit something harder than they are and are dull on one side of the chain.