A great instructor can make a world of difference in your confidence level -- in both your own skills, and in the capabilities of the airplane.
I once signed up for 10 hour package with pilot-extrordinaire Ed Nelson of Sidney (Cabela's home) Nebraska. Ed grew up right there as crop duster, flies nightly for FedEx and during the day runs the Sidney Muni airport and teaches aerobatics. After putting me through 6 hours of short, soft, & steep landing work on his old farm strip, we went up and spent several more hours doing spins over the top, underneath, the falling leaf thing, etc. He really taught me just how controllable a cub really is -- balky occasionally, but predictable.
Steve: maybe we could start a directory of recommended instructors with tailwheel/cub experience from around the country. I'd put Ed on the list with 5 stars.