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Thanks for the detailed reply.
This definitely seems doable but not easy, especially given that I would be guiding a non-coder person through the process via skype or something like that.
I found a couple of threads and other sources talking about X11 being necessary for Perl/Tk to work on OSX. Do I not need to worry about this?

My googling led me to ActiveState's perl dev kit, which supposedly includes a tool that can generate standalone OSX executables without access to a mac computer. There's a 21-day trial version so in principle I could just do this on my own (Windows) computer for free with little fuss. Later updates would be a problem but even if I only get one release out, that's better than nothing. This is free software I'm writing as a hobby so I couldn't justify buying PDK - but maybe a couple of OSX users would donate the money.
So, does anyone have experience with cross-platform packaging in PerlApp? Does the trial version have limitations in addition to the 21-day trial period?
Edit: it looks like the executables generated with the trial version of perlapp have a time bomb in them. So the trial version is only good for testing, and the full version is not that cheap. Looks like I will be trying the remote-control-the-mac-guy-to-run-pp-for-me option. I will almost certainly come back here with questions if (when) we get stuck.

In reply to Re^2: Perl/Tk and PAR::Packer on OS X by elef
in thread Perl/Tk and PAR::Packer on OS X by elef

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