If he were mine I would pull the shoes and get a pair of well fitting boots and use them only for walking to the arena. They would last a looong time doing this and would pay for themselves over time vs. the cost of reapplying shoes every 6-8 weeks.
I'm not against shoes but keep my horses barefoot and boot as needed as I dislike the inconvenience of them throwing a shoe, one coming loose etc. Especially since my farrier lives over an hour away and it would be a long wait to get a shoe tacked back on.
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