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.