for your first one.. build a lip. it will make it alot easier.. and urbans are usually really sketchy to begin with (for me atleast) .. and for a first timer a lip can take some of that sketchyness away
no, i knew this guy who sold his skin to buy new skis, and a pop corn maker. he did alright, but every morning, he had to wrap his self in seran wrap to hold in his insides...
yeh if it is like a handrail for midgets...in that case you can just ollie onto it...but chances are you are goingt o need a lip becasue it is hard to ollie super high onto an urban rail and grease it first try...the first time i was doing real rails was on an urban style lip on a down rail...the lip got so bad that at one time we were just ollieing right onto it...ollieing onto a rail from the side like that from flat isnt as easy as you think....but you do have a point if it is low enough.