Besides the obvious "cool factor" & the added challenge of tailwheel gear, another thing to consider besides drag when removing the nosewheel is the de-stabilizing effect. My own C150/150 taildragger sure yanks & banks in a sportier fashion than I remember a stock 150 doing.
Personally I think most people who are into Cherokees would not be interested in a t/w conversion, but maybe I'm selling them short. But then again, if you're a low-wing fan....there's lots of high-wing taildraggers, but low-wing taildraggers don't seem too common, esp 4 place ones. About all I can come up with off-hand for 2-seaters would be Swifts, and for 4-seaters the old triple-tail bellancas. I'm sure there are more, but none that I can think of that you see with any regularity.