tailwheel conversion
Personal opinion on tail wheel conversion go for something like the Supercub. The Chipmunk is a great aircraft and an excellent trainer but the Supercub is lighter and is more sprightly.
I am still learning on Chipmunks and love the character. Not going to enter the brake debate but the one I fly ise set up with just a little brake right at the extremes of rudder travel. This isnt right and on some cross wind take offs having brake applied when you least want it isnt good.