I already know python and Flask but I have this burning desire to switch over to Ruby on Rails. Everything about it seems so appealing and time-saving, from the documentation to the quality of support sites like rubygems. Flask/django have nothing like this and are such a mess in comparison. Is learning a new language/framework worth the time investment or am I just addicted to wasting time?
Rails and Flask are apples and oranges; something like Sinatra would be closer. There's no way to know if it's a "waste of time" because we don't know what you're doing or why. There are more Rails-like frameworks for Python.<p>If you have a "burning desire" to learn something, then learn it. But the notion that it'll magically make all your development easier is a pipe dream.
You should always be learning something new. If this is what peaks your interest, do it. In a month come back and see if you want to make the switch professionally (assuming this is your day job). The worst that'll happen is you'll know something new.