The kind of cheap portable pull through sharpeners that you'll most often find have this major flaw that not a lot of people talk about. Whether they use ceramic or pieces of carbide or whatever, they tend to be staggered such that one side of the V is in front of the other. This makes it so that you can't reach the whole edge on both sides with most knives. There will be a section on one side of your edge at the heel which the pull through sharpener never touches. As you can imagine, repeated use of the pull through sharpener ruins the uniformity of your edge at that section.
Carbide pull through sharpeners can also end up shredding your edge, and the ceramic ones will create a fragile scratch pattern which is parallel to the edge. This weakens the edge. You want the scratch pattern to be at least diagonal or perpendicular to the edge.
Short takeaway is that pull through sharpeners generally don't do a good job and they make more work for you in the long run. The way that you know you're doing a good job sharpening is when you have reduced the amount of sharpening that you need to do overall. With pull through sharpeners you need to use them more and they give you poorer results. With freehand or a sharpening rig, you can do a much better job than the pull through does, and you can go longer without needing to sharpen again. And then the final, best way in my opinion, is if you just touch up your edge a little bit after each time you use the knife, and in this way you will spend a lot less time overall having to sharpen, because there won't be any chance for edge damage to accumulate which would have taken more time to fix when you eventually got around to it.
And this last bit is just my personal thoughts on a slight tangent, but all this potentially goes out the window if you are working professionally with knives in food processing. In that case, using an electric pull through sharpener and a honing steel might actually make a surprising amount of sense...