Your skate board you describe is a very small hover craft. Your cylinders, board, and you will have to be lifted by the pressure under the board and the skirt around the board will have to retain enough pressure to lift you.
The skirt is around the circumference of the board. I work in pounds so bare with me. At one PSI and the board and you at 200lbs. That means 200 square inches of board, say 10 X 20 inches = 60 inches of perimeter or skirt. Say a average on flat ground of 1/4 inch gap at 1 psi or 15 square inches of air lost at 1 psi on very flat ground.
Your air would not last down the block. At 400 square inches of area and 1/2 PSI 10X40 you now have 100 inches of skirt or 25 square inches of air lost at 1/2 PSI.
Now in the real world if you could stay on this air bearing (think soft no friction ice) expect your air loss to be many times that say 10 or more. every crack, lip, uneven surface will rob air even if you could keep it level.
If you do try this, get a harness and tie it off from above because you will bust something on the concrete. Your center of gravity is just below your navel. your ends will try to swap. Oh ya gravity will move it down hill, you have no steering. It will seek the low spot regardless of the vector it started on while your mass tries to continue on.
Dats Y
Brad
__________________
(Larrabee's Law) Half of everything you hear in a classroom is crap. Education is figuring out which half is which.