Not in my experience, unfortunately. The reps we got with GCP could give us advice, but no real powers to push stuff or solve problems, it felt more like L1 support. As described bellow, maybe it depends on a company size and/or a country.
I don't agree, I'm hosting my email myself on a Debian VPS with installed http://iredmail.org/. I have unlimited domains, customizations, full control and there is virtually no maintenance needed, just regular updates.
RoR is a lot more widely adapted, so it's better choice for your career (than Web2py or even Django). But I don't like it, because I find it bloated (like a slow and fat man) and overcomplicated.