I have both a leather punch like this
And a set of leather punches like this that you use with a hammer
For putting more holes in the leathers to shorten the stirrups on a western saddle, I have to use the latter because the first one won't reach to the middle of the leather. I've never been able to get clean holes with a power drill, even if I was using a new bit.
Something you might consider, though: is there enough space to punch holes to shorten the leathers enough without compromising the mobility of the leather and "trapping" their leg in a certain position? If the fenders are too long, then there is only so far that you can pull them up to the tree and only so far that you can pull the stirrup up before they start looking like this and make riding very
If you can't shorten them enough without making them look like that, then you might be better off searching for a smaller pair of fenders/leathers like this and switching them out.
Or, buying a set of leathers without any fenders on them so that they would basically just be a strip of leather about 2 inches wide that is 100%, fully adjustable to the exact length you need. Western Stirrup Leathers - Vertical punched for Blevin buckles Western Stirrup Leathers - Horizontal punched for Al-Ray or Blevin styles
Doing that would make the stirrups look more like those on a plantation saddle
Or and Australian stock saddle
but they would work well.
As for those little buddy stirrup things, I suppose they would work in a pinch, but if you want your child to learn to ride properly, then they'll be a bigger pain than they're worth. Because they attach to the saddle horn, they are basically guaranteeing that your child is forced
into a massive chair seat position because they won't be able
to get their feet under their hips to ride correctly.
I like the position that these put the rider in, but I wonder about stability with the elastic around the cantle Saddle Sidekicks - Saddle Adapter for Kids