When to give up?

You could use glue on shoes or a different brand/style of hoof boots - there's a lot of variety between them now and it's quite horse dependent what suits, a bit like some brands of rugs just never fit some horses
 
If you don’t want to re shoe (for whatever reason), and the horse needs protective hoof boots to hack comfortably, you simply need boots which do not also attach around the fetlocks, like Flex, or G2s with their figure 8 strap.
You need a different type, very simply: a boot that generally stays on with your horse’s paces, but spins straight off when detached, rather than remains anchored and flapping round his ankles!
Obviously, you will then have to find the damn thing, one reason garish colours are now so popular.
Can be a pain trying out boot shapes and styles, basically the best boot is the one which fits your horse, but the safety considerations described are equally important to both your enjoyment.
Doesn’t sound like you’re ready for the Tevis Cup yet - there are plenty of other hoof boot styles, including older, more ‘clumpy’ designs which would answer just fine for hacking about. Good luck
I use Equine Fusion hoof boots and they never come loose or come off. No extra straps to hold them on if they come loose. I highly recommend them.
 
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