My experience is similar to TrailHorseRider: after riding 5 years in boots, only once a boot came off and was found later. No loss. I train for endurance so there is a fair amount of trot-canter in my rides.
I also boot in the front only, when they are freshly trimmed and on longer rides on hard surfaces-gravel roads. Otherwise, later in the trim cycle, they usually go bare comfortably.
My preference goes to Gloves and I have an array of sizes to accomodate changing hooves. A good investment, the first pair I bought is still ok (became a winter boot with studs). Then, the Renegades are close seconds in my favorites. Then the Epics. (also became studded winter boots). Vipers on my wish list...
I wouldn't go barefoot to save money though. To have a happy horse bare, it takes dedication: a look into feeding, management, footing etc. You might save if you learn to trim yourself, with a professional once in a while to correct things if needed.
Good luck RhondaLynn, let us know how it goes.