Except Cessna already tried it and the test pilot almost endoed the plane when he pulled the massive Fowler flaps...it needs the bigger tail.
I've always kinda wanted a tailwheel '64-'65, but only with the 140's tailfeathers. Now, that would really look like a baby L-19/O-1 Bird Dog! It wouldn't be hard to do, by using the 140's tailcone to mount them properly (and it comes with a tailwheel already)!
Approval through 'normal' channels might be a little iffy, but I'm sure it can be done.