But you are going to find people in the Python world telling you to abide by PEP8. And saying that you should be using virtualenv. And saying that you should not use (module-level) globals. And saying that you should be using various checking tools. And the checking tools may say annoying things (some of which will be good points about your code).
And I'm kind of one of those people, as well; not saying that there aren't reasons to break a rule, or that it instantly makes your code crap if you do, but I understand these arguments.
And a vocal number of those on Python IRC channels tend to be dicks to newbies or people with unusual ideas.
So I guess I would question whether Python is going to give you what you want. I can't speak much to Ruby's culture.
Use the tools you like which make your life better, and if it makes your life better then ignore other people's unsolicited opinions on the internet and just do your thing.