It's very individual what they can do and adapt to. I kept Crow barefoot for a long while on various grounds, but when I started riding him more I had to shoe him. He didn't get sore by the ground, but he wore his hooves down to the point that made him a bit sore. I didn't feel there was much point in trying to make his hooves adapt to the surface we ride on since he had been barefoot for years already. I like barefoot when it's possible tho.
Our draft has bad feet, if he goes barefoot he'll get sore on grass even. He's good with shoes tho.
Remember to pay attention to your horses feet even more if they're barefoot, especially before you know how much he can do. The hooves adapt some to the ground they walk on, but they can only do it so much and it takes time. So shoe him before he gets sore, if you notice that he wears the hooves down way more than they can grow, and be careful about how much pain he has to go through in order to toughen his hooves up on rough ground.. it's ok to some degree but not too much. :)
I know barefoot horses tht can do anything a shoed horse can, plus they don't slip on concrete as easily.