Brandon--YOU ARE RIGHT ON THE MONEY!!!!
I am a sailing instructor and licensed Master. The best way to learn how to sail is on a small boat with a tiller. My preference is for small keel-boats around 22 feet. In general (there are exceptions of course) it has been my experience that sailors whom have learned the basics on a small tiller boat grow to be better sailors. When I teach the advanced classes, the students who learn on a tiller tend to do much better and are more skillful/confident on the bigger boats.