It turns out that even getting Ruby to link up with that Tk installation (which is a VERY nice Tk installation) is a bit challenging in it's own right.

wxPerl is definitely portable enough. I don't neccessarily need something that is trivial to install, but if applications work in Windows, Linux, and MacOS after jumping through minimal hoops, it's all good :) I haven't played with wx in about a year (and then it was only explatory), so revisting it makes sense.