I haven't run barefoot in a while but for what I actually started trail running before I did street running (the opposite of what most people do, ironically) and I ran into a similar problem in that I thought that my feet were plenty toughened up and able to run on street ... instead I suffered through a "re-conditioning" period which was somewhat surprising.
the bottom line is that trails surfaces are un-even, irregular, unpredictable but also yield a lot more than asphalt or concrete.
So a trail surface will beat the hell out of your feet and soles especially but will (surprisingly) not really punish your ankles or the bones in your foot (unless of course you step on a root or a really sharp rock ... ).
On the road (I noticed), it was the opposite. Really easy on the soles but due to the fact that the surface is harder and somewhat flat it takes a lot out of your calf and tendons than a trail surface wouldn't do.
That was my personal experience ... each one of us is different, so take what I said with a grain of salt. It might not apply to you.
I thought maybe it was just me, but I was noticing the exact same thing. I run on trails and can go 5 miles without pain, then I go run on the road for 2-3 miles and notice something hurting before long. I prefer trails, and am willing to drive the 15-20 minutes to get to the closest trail, but when I'm working and don't have much time between shifts I'd rather just run on the road, but am finding it difficult to build up the mileage.
Do most runners just stick with one or the other? Or does everyone do some of each? I'd like to get in more weekly miles by running on the roads around my house, but it seems I can't go very far anyway.
