... He will tip toe over small stones when ridden, go weeks and weeks without needing a trim..
There are four reasons to shoe a horse.
Your opening description just defined reason number one; 'Protection'.
He is a little flat footed, and it's never bothered either of us working, I just have always has this question in my head 'to shoe or not to shoe'
It might bother you if roles were reversed and you had to carry the horse around on your back for awhile.
He's flat footed. That predisposes a horse to tender feet over challenging terrain as evidenced by your assertion that "he will tip toe over small stones...".
Wear exceeds growth (also a reason to shoe), as evidenced by your assertion that, "go weeks and weeks without needing a trim".
In short, you've answered your own question. Your horse would appear to better meet your use expectations if he were shod.
Recently the farrier cut in to the bottom to create an upside down v so there was no pressure on the crack to make it go any worse.
Sometimes this works; often it doesn't.
But his hoof looks a bit bruised.( been bruised since he done the crack, possibly galloped on a large stone or kicked a fence ??) the severity of the bruise has gone but it looks a pale pink on a wider scale.
Happens all the time and more visually evident if the horse has a light colored hoof. Usually no big deal.
Bracken is brushing his back legs in the field, but not ridden. ( bruising in on the outside of his hoof) and he is also over reaching. I was turning him out with over reach boots on, but the daft thing lost 1!!! And I have no idea how!!!
Brushing; over-reaching; tearing off bell boots; tender over rock. I'd guess excess toe length. Given he "goes weeks and weeks without a trim", the excess toe is likely all forward running distortion and accompanied by dorsal wall distortion. In other words, someone is trimming the bottom of the feet but not addressing wall distortion by dressing. Horse ends up with overly long, dishy feet; d/p imbalance and.... brushes/interferes.
Is this horse gaited? Perhaps a Tennessee Walker?
If I can I will upload images of his foot/frog.
I only ask because he is coming to be due a trim soon and I am thinking of a barefoot trimmer. She very good and been recommended via a few people on my yard. She has also seen bracken and said he has good feet. But to me it looks as though the underside of his foot has changed shape with depth an flatness.. ( hacking in the area is road work)
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Sure, I'll comment. Why would anyone employ a practitioner who intentionally limits their hoofcare education and experience to less than required of most farriers in their first 30 days of training?
Worse, you're located in the UK. Barefoot trimmers are recognized in that area as being so poorly educated/experienced in equine hoof care that they are forbidden by law to do anything more than just a trim.
Select an experienced, full service farrier that can meet ALL the needs of your horse; current and future. Licensing requirements in the UK for hoofcare practitioners are tough and produce a necessarily high level of farrier quality. That law is intended to protect you and your horse. Just to give you an idea of how strict those legal, educational requirements are, the lower class Associate Farrier in England is considered equal to the top AFA journeyman farrier certification in the United States.
Avoid the charlatans and leverage that legal quality requirement to assure your horse the best possible care it deserves.