cantor, personally, when in front of several options, I ask myself this
question: Which of these technologies have the best freedom-supportive
community?
I have to say I try to avoid projects that call themselves open-source,
because, in my experience, they always end up sacrificing freedom in some
way. For example, they recommend non-free software in their documentation,
allow non-free packages in their repositories, etc. You can expect their
communities to do the same.
I was learning Ruby when the project was called "free software", but I
stopped when they change the definition to open-source. I don't go often to
the Python and Java neighborhoods because of their orientation towards
open-source too.
Recently, I was also looking for a language to start learning more about
programming. I found GNU Guile, which is a Scheme implementation for the GNU
project. Being GNU, freedom is first, so I'm learning it. At first, I was
concerned about its community (or lack of it), because I've never heard of it
(how long took you to hear about GNU?), but then I came across the Guix
System Distribution and found that their developers are using Guile Scheme
for writing pretty much every component of the system, from daemons to
libraries to user interfaces and package definitions. I think this is the
right tool for me. Maybe it is for you too?