Though I much prefer barefoot, it is not always an option. My gelding is barefoot year round and does awesome, same thing for our older gelding, Our mare had a set of shoes put on for the competitive trail ride. My stallion, who has really good feet still gets ouchy....I keep him barefoota all year, and ride him as far into summer as I can stand, but when his ouchy ness interferes with training, I have shoes put on. He usually ends up with two, six week sets a year, barefoot the rest. Last year we had pretty strong trasitions between hot dry/ soggy wet weather on pretty much a daily basis that played havock on their feet....my geldng who had never needed shoes in eight years went lame for 6 weeks from severe bruising!
So...getting to the point...sometimes you need shoes. One thing that my farrier suggested was to get them used to the nail tapping feeling by picking up a rock and tapping on the foot in the area were the nails would be driven every time you pick out the feet. Their feet are very sensitive to vibrations and it is an uncomfortable sensation that takes some getting used to. I also think you need a patient and understanding farrier to make it work ;).