I have travelled more than one road (not through indecision but due to a mixture of platforms).
On the Windows side I've been using Activestate Perl, which has worked quite well. I keep the script open in an editor, and a command prompt session open for running it. I've found that MacPerl works well on the Mac OS (8.6), and I've found that the scripts I wrote on there ported with no changes except to the shebang line, when I moved them to the Linux box, or to Windows. I think this is a huge advantage to Perl -- it's quite portable. Naturally, there are the usual file-naming and line-ending issues.
<digression>
I have helped my spousal unit with his VB projects. I deeply dislike VB's built-in limitations, but that is another rant.
I do wish that I had a development environment like VB's for Perl, which would show me immediately when I commit my favorite stupid mistakes (e.g. dropping a semi-colon or using InStr instead of index, handicaps which come with using more than one system/language). I think I once read rumors of such a thing and I hope it is coming (although I went for years debugging C at the command prompt. Have I gone soft?). And yes, I still type 'ls' in the Windows command prompt, and 'dir' on FreeBSD... </digression>
I have searched for a gui front-end for Perl, and have worked a bit with Perl/Tk and with wxPerl. They have both worked well for me, but I didn't find a way to design things graphically like in VB (I'm not saying it doesn't exist, only that I didn't find it after a brief search).
Knowing the C programming language has helped me to learn Perl. (Although I still love C, I would probably learn Perl if I were just starting out today.)
I hope this helps a bit.