Activestate Perl is alright, but its lack of maintenance of PPM packages and ...

I use Ubuntu on my own computer, Red Hat on company servers, Windows/ActiveState and Windows/Cygwin on company desktops.

I must say ActiveState has become very nice the last couple of years. No matter what OS you choose, the relationship between CPAN and OS distros is an issue at some point, more for those that habitually tries very many different packages all the time. Usually that is not a problem google can't help. Sometimes it is. Not a big issue. Note that there is suplementary repositories for most distros, including ActiveState.

That off course, does not mean that I shouldn't soon try out Strawberry, I will...

Edit: Almost forgot: If Ubuntu is OP's favourite, I would try to find out if Wine was a viable option, or if running windows and flightplanner in VmWare is. If not, I'd go for dual boot.