Wild horses don't get dentistry either, nor does anyone do anything with their feet. So there is no benefit to those things for domestic horses???
(e.t.a. -- to add to welsummerchicks' list of reasons to clean, I'd add that I've seen quite a number of cases of chronic tail-rubbing solved NOT by worming or Listerine but by sheath-cleaning)
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IMO if you have not done their sheaths thus far, it is worth picking an auspicious and convenient day and going after it at least this once so you can see what the real situation is down there. If they are clean and beanless and have nothing suspicious anywhere, it is kind of discretionary how often you want to do it again. If they turned out to be cruddier than you thought or have a large bean or have any sort of condition that makes you go Hm (lumps, bumps, etc where they shouldn't be) then it is a pretty reasonable idea to do it yearly. I have known a couple of horses over the years that really require it more often.
Oh, another situation where it is worth doing them at least once a year and preferably more often is if you have one of those uncommon geldings who, pastured with mares, will not only jump them but actually complete the whole act (except obviously for insemination), since if they are going to be USING the dipstick it really ought to be wiped clean from time to time b/c I've known mares to get nasty uterine infections that way. Most peoples' geldings don't do this, of course, or lack the opportunity, but there are enough exceptions I thought I'd mention it.
As to the "how to do it" part of your question, as you can see from this thread, it depends on your horse. Basically, some horses will let you have your way with them to whatever extent you require, with them just standing there. For those, the procedure should be fairly obvious -- pick or wash off the external crusties, then winkle a short-fingernailed finger into the opening at the end of the organ and feel around til you have figured out that one direction is the urethra and another direction is the little blind pouch that the bean can form in, and if there's a big bean there then get it out by whatever means seems workable. Or as RoPo says in some cases you can just kind of work the bean out from the outside.
Other horses won't let you do that. For them, either you roll your sleeve up and go spelunking (see previously-posted link for a post I wrote a long time ago describing more or less what you will do and find), or you wait til the vet can tranquilize the horse so that he dangles and you clean him externally as described above at that time. A few people will have the vet tranq the horse *specifically* for sheath cleaning; more often, it is something you do when the horse just happens to be sedated for some other reason e.g. stitches or teeth. Do be careful when cleaning a sedated horse, as depending on what drug is used they sometimes retain lightning-fast reflexes and you do not need your head kicked off unexpectedly.
If a horse just absolutely flat-out won't let you mess with him down there, it is not likely that he will curl up and die of it. That said, even though the number of problems avoided by sheath-cleaning is small, it is still SOMETHING and IMHO worth doing. And, as I say, how often to do it can depend on your individual horse. Some get super gross super fast, or have suspicious things you want to keep an eye on. Others make you go 'and I'm doing this again this year *why?*'
JMHO, good luck, have fun,
Pat