I wish I had more pipes that didn't cake up. For me, I really started getting more cake when I started slowing way down. I think that the slower you smoke, with a smaller diameter cherry as you smoke, the more it pushes the oils off onto the sides of the chamber. But, I do have some that cake like a MF'er. I am constantly rinsing and wiping after each smoke to beat it back, but... sometimes cake just happens. I would prefer mine not have any.
If the pipe has made it through 150 smokes without damage and without caking, it is safe to assume that it will smoke just fine. Proceed without fear.