Hey Araun,
My feet definitely have gotten a bit smoother. They seem to be getting more tolerant on rough/pointy surfaces but they are more pliable than they were when I started (and I'm a relative new BF runner so, I'm sure my feet will change more over the next few months).
As far as your question about how to extend your runs, I'd respond that you need to take it very slowly. I know it seems like a step backwards, but my advice is to remember that you'll need a few months to build up to where you're ready to do longer runs (especially on rocky trails or rougher terrain).
So, if you really enjoy trail-running, keep doing that. Start out without shoes and run or walk for 1/2 mile at first and then finish your run with your shoes on. Next time, do the same thing and, if after 1/2 mile you feel o.k. then add just a bit more (maybe 1/8th of a mile). Don't start with shoes and then finish BF as your feet will be soft and tender from being enclosed in the shoes and you'll undo the work you've done so far on building up your pads.
Go slow to go fast. If you're running on tougher terrain and trails then it may be slower going at first but you'll be building stronger feet quicker too.
Be patient Araun, listen to your feet and have fun.
Kelly