I wanted to do them in number order, so I followed STS-1 with STS-8, STS-41C, and STS-51A. That was a steep difficulty curve, but it didn't cause me any significant problems. Of course, this was in NOVICE mode, but I still had to negotiate relatively complicated tasks like station keeping with orbiting objects, grappling satellites without the help of provided joint angles, use of the MMU etc.
I am currently waiting for the next service pack to be released before I start my eleventh mission (STS-93 Columbia).