Because I live where there is much snow in the Winter, I was pulling my horse's shoes in November, and putting them back on in April. 2 years ago in April, I thought, "Why not just leave them off?" So I did, and have never looked back!
My farrier said "Even 1 nail compromises the integrity of the hoof wall, so if your horse can go shoeless, DO IT." I trail ride. Initially, there was quite a bit of chipping. But after the hoof that had had nail holes in it grew out, the chipping stopped. It is nice not to have to worry about him throwing a shoe! Now, after 2 years, my horse rarely needs trail boots. His feet just keep getting stronger and stronger. The boots that I used were Easy Boot Trail. They fit well, and have never come off, even when gaiting.