G'day maria80e,

To answer your first question: yes, this is entirely possible. I'm running Win10 and currently have five Perls installed: ActivePerl 5.16.3; Strawberry Perl 5.26.3 and 5.30.0; Git Bash Perl 5.26.2; and, Cygwin Perl 5.30.0.

I recently ran into some issues installing a second Strawberry Perl (the 5.26.3 one). I asked about that here: "Strawberry Perl - installing an older version" — I received a lot of advice, some of which you may find useful.

I see your second question has already been answered: "Re: How install multiple version of perl".