I haven't tried installing multiple versions/distros of Perl on a system, so I can't offer any tips or pointers on that topic.

Although I have to have Cygwin on some systems at work, I haven't installed Cygwin on my personal systems and haven't done much with Cygwin's Perl.

Strawberry Perl is going to be closer to the "Perl on Linux" experience than ActivePerl - at least it will be immediately after install. Both can use cpan, but Strawberry Perl (32-bit) already comes with the compiler and other needed tools for compiling and installing modules from cpan. ActivePerl can't compile modules straight out of the box, but you can use the PPM utility to install the needed items from ActiveState's repository.

Also, Strawberry Perl offers a portable version of their distribution that doesn't "install" anything. Instead, you run a batch file that opens a new command prompt and sets the environment variables of that command prompt to point to the needed folders to use portable Strawberry Perl. This can be put onto a USB thumb stick drive so that you can run Perl from that USB drive on other Windows systems - even if they don't have Perl installed.

Another alternative is DWIM Perl, which is Strawberry Perl 15.4.2.1 RC (32-bit) plus a bunch of other modules installed and includes Padre.

I haven't used it myself, but another popular distribution for Windows is Citrus Perl. The folks behind Citrus Perl also make the Cava Packager utility that can bundle your Perl script into a stand-alone executable.

As for which to use, I think that's a personal choice. I started out using ActivePerl. Lately, I personally have been using Strawberry Perl and DWIM Perl. It might be a good idea to try a few of these out to see which one you're more comfortable with.

The above information is based on my personal experience. Good luck with deciding on which distribution to use.