A: Good question, but “several” cigars? Unless you’re exaggerating, something is wrong with that picture, or you’re buying really cheapo cutters. A good cigar cutter should last at least a year or two depending on how often it’s used.
It could just be gunk. Over time, gunk forms on the cutter, which can cause it to cut poorly. If that’s the case, try cleaning the blades with alcohol. That and a few cotton swabs will easily remove all the gunk. If you’re a “chomper” (like someone I know), and have to clip-off the messy head several times during your smoke, that will gunk-up a cutter pretty fast.
If the blade doesn’t cut better after that, the problem may be the cutter’s blade/s. If it’s a Xikar cigar cutter (shown), their warranty states: “Should you ever have an issue with your cutter, simply return it to us and we will repair or replace it for you. (Lifetime Guarantee!).” Just make sure you’ve got a good backup cutter while they take care of it.
As for sharpening the cutter yourself, if it’s a plain vanilla double blade cutter, the only way to get to the blades would be if the cutter housing was screwed together. If the housing is glued, forget it. Even if you could get a cigar cutter open, I’m not sure how you would sharpen the blades yourself.
Maybe some of our readers have some solutions for you, too, and will leave a comment.