If you are cutting mostly all softwoods those sorts of file-holder hand guides are good enough. If you have much hardwood like I have cut for the last thee decades, you need an accurate system. I was never much good with the hand guide like that. I use one just for touchup in the field, but that's all. Now, except for the files themselves, the Oregon brand tools I have tried have been of low quality. I tried the "Timberline" sharpening jig but I did not like it. I have been using the "Granberg Bar-Mount Chain Saw Sharpener, Model# G-106B" for quite some time in my home-shop. They also make a similar tool that uses a 12 volt powered grinder (G1012XT). It holds the file precisely at both angles.
The way I get a chain really sharp, particularly if you have hit a rock or such, is start with a dial caliper and measure the length of all the teeth to find the short one. Using the Grandburg I set it up and sharpen that one tooth. I then measure it and sharpen all the rest of the teeth to that length. When they are all the same length they are also all the same height. It does sound like a lot of work, but it is effective. I learned the measuring trick from a professional lumberjack.
I harpened our fire company's saw and the enxt firefighter who used it said it was the sharpest re-sharpened saw he ever used.