There's a guy I know who thinks most taildragger pilots are sissies.
He has a Europa monowheel.
Ha ha. But it's still a taildragger. I used to own a Fournier RF3. I often successfully negotiated 50% discount on landing fees as it only had one wheel!
I quite liked the Chipmunk, I just think that the Bulldog is a much nicer aeroplane. Better view, easier to manage, better power:weight... If it was tandem seating, it'd be close to perfect!
With about a thousand hours on the Chippy and less than a hundred on the 'dog, I'm bound to be biased! And I only flew the Bulldog at CFS and never in anger with a real student. The qualities you mention were an improvement on the Chippy, particularly the power. But I never liked side by side for a military trainer, and the stick with the left hand was a disadvantage. It's was easier to fly (apart from the way the RAF contrived to use the CS prop) but this isn't necessarily a good thing. The RAF used the Chippy up to 1993 at EFTS, which still had an element of grading, and for that the Chippy was brilliant. It had it's problems - a prehistoric engine, limited crosswind capability and maintenance issues. But we still used it in preference to it's replacement. And neither of the two aircraft that followed were as good as pilot trainers.
Why haven't we been able to evolve training aircraft at the same rate as the rest of the industry? Could be a good subject for a paper!