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Remember that there are a lot of different things all frequently called "hackamores" just b/c they're bitless -- but that are really apples, oranges, grapes and pineapples
First you got your sidepull type things. Also includes snapping a leadrope to both cheekrings of a halter. They provide a direct, unadorned pull on the bridge of the nose, nuthin' else.
Then there are mechanical hackamores, the ones that have leverage shanks and some form of curb strap - basically like a bitless curb bit.
Gag action can be worked into any of these. The Bitless Bridle (in a trademarked sense of the word) in essence has very mild hackamore-gag (pulley over the poll) action; some of the western or jumper-ring mechanical hacks have quite significant gag action.
Then there is the bosal, which is sometimes spoken of as a hackamore; and probably other things that are not coming to mind at the moment.
These different things have fairly different actions on the horse (for example, you can direct-rein quite effectively in a sidepull type hackamore but not so well at all in a curb-type mechanical hackamore). The ones with thin bearing-surfaces and substantial leverage (and sometimes substantial pulley action as well) can inflict considerable pain on a horse when pulled on hard, just as comparable types of curb or gag bits can.
My experience is that it can be hard to fit a sidepull type hackamore so that it does not chafe the nose in long use (the rope-type nose ones rub and can be rather severe, and the ones with a leather or padded strap still seem to wear the tender nose-hair off a lot of horses, same as prolonged halter-wearing can). Some horses can wear them ok, chafing-wise, but they are just a really dull crude means of communication. And the leverage types do not offer very much opportunity for real communication beyond YO HORSIE, STOP DARN YOU (plus if the rider should, even accidentally, pull hard on them, like if you get set off balance for a minute, it can really hurt the horse).
AFAIK anything bitless is still prohibited in hunter showing, certainly in dressage. You can use something bitless in the jumper phase of eventing but I am not sure you can use it XC and you sure can't in the dressage phase.
"Can a horse be trained to carry itself round and on the bit"? Sort of kind of, partly, not really, yeah in a way
The thing is, that's only partly produced by training - it's largely from RIDING, moment-to-moment. I have yet to meet anything bitless that affords nearly as versatile and subtle and useful communication with a horse as a well-fit well-chosen bit. Bitless arrangements reduce your reins to the level of "me tarzan you jane, want slow down horsie?" rather than permitting you to ask "please stretch the top of your poll for a moment" or permitting the horse to indicate to *you* "I am in the very earliest moments of finding this difficult and losing my engagement". That's the thing -- the bit is not supposed to be your steering or brakes (not once the horse is reasonably well trained), but tht does not mean it does not permit OTHER very important functions)
Personal opinion: fine for quiet trailriding or just schlepping-around-for-fun on a WELL TRAINED horse, and good if you have to put a person of unreliable balance or hands on a horse that's at least well-enough trained to remain controllable. But I just prefer to have a better 'two way radio' so to speak with the horse. CAN you ride bitless? Sure, of course. Can you produce some semblance of roundness, collections and extensions, etcetetera? Of course, if you're good enough. But can you do as MUCH in that regard, as WELL, as with a bit? IMO, nope.
(edited to add: there are a few horses in the hunter ring, at least, that are EFFECTIVELY being ridden altogether bitless. The rule says the horse has to WEAR the bit, it does not say the rider has to USE it, and there have been a few (rare) adequately-successful show hunters who were ridden about 99% off leg and seat.)
Pat