Why CLI? Even vi has a GUI (so I hear)... so does Emacs.
And Komodo runs under Linux, giving you Perl & Python in a GUI.
As for porting from VB, there once was something out there to interpret VB, but it was pretty poor... I thought I got it from CPAN, but I don't see it there any more. Inline::VBASIC or something similar.
Plus, there's the option of "staging" the transition. Teach Perl, leave the Win32 box up, gradually move things over as they're rewritten. I've worked in (several) shops where the migration from Win32 to Linux was carried out by making rewrites of each module in the schedule...
Don't forget about VNC. VNC's Java plugin is an easy way to get access in "GUI mode" to your server (over the LAN, unless you're using SSH and have bandwidth to spare!) from non-Linux workstations.
(Linux || Unix || Solaris || Irix, &c. ad nauseum)
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