JAFO,
Superb post. If you haven't done so already, have you thought of publishing it? It might read very well in the PFA mag or one of the other three. You captured the essence of it very well, I thought.
Starbucks, BigAl,
You're definitely not taking on too much at any point. Remember that, until the 152 in the mid-60s (?) ALL basic pilot training was done on tailwheels, from hour 0!
For me it opened up the door to the Pitts, which was always the point, but, unexpectedly, it opened up much more basic and interesting flying that I've enjoyed immensely. I'm not all that interested in the equipment and environment that comes with more advanced aviation. I much prefer the basic, grass-roots, park it under a tree type of flying, low and slow, watching the world go by close up. When you spend enough time in one airplane, you won't need any of the already-basic instruments at all but you learn to fly it viscerally, using all your senses at their peak awareness (course, that's partly true for most airplanes anyway).
I haven't flown anything with a nosewheel in about 8 years and, while it can be interesting and more practical, I don't miss anything about it.
Go for it and at least you can critique the exercise afterward having done it, rather than sit at the front of the door having never gone in (or some kind of metaphor like that).
Pitts2112