If you are regularly biking twenty miles round trip, you should be able to do a twenty mile round trip without difficulty. I used to have a ten mile each way work commute, as you do now, and on weekends was able to easily bike 60 miles in a day, 100 miles if I pushed myself, and I'm in a pretty hilly part of the country (Pennsylvania). As for fairly busy roads versus bike trails, I find it much easier to put in many miles on the roads, rather than on trails. Go for it, dude.