One plane I would like to mention is the Hangar 9 UltraStick. It is a shoulder wing that has setups for tricycle and taildragger gear. You may need to duplicate the plywood gear doubler so you can switch it easily. That way you can get used to a faster and more aerobatic plane before you transition to the tail dragger. I have a set of plans on the way from RC Modeler for the original version (Das Ugly Stick) and plan on setting it up for both.
After that if you want to try a warbird, try the Great Planes P51 Mustang. It has a modified airfoil designed off of the UltraSport. I have heard that it is a floater but flies very well. I haven't flown it yet so I cannot attest to it being easier to fly than the Truer to scale warbird planes out on the market. I have a kit laying under my bed itching to get built.
If others don't think the Great Planes Mustang is a good transition, you can go for the SuperSportster. That will get you ready for the speed and aerobatics of the warbirds.