If it's Win32 only, you should consider writing it using Win32::GUI instead of Perl/Tk. It's very easy to write code for and the widgets are Win32 native, unlike Tk. It's probably not as full featured as Tk but I haven't run into any brick walls yet that can't be overcome with a little creativity. I'm using it together with perl2exe and it's working well.

I also host a mailing list for support of the Win32::GUI module.