I'm looking for information on what is easier to use? Going to last longer? Will help my development career? Ease to deploy?
Any other helpful tips are appreciated. Thanks
Having built enterprise applications in Rails and Django, I would recommend Django over Rails 99.999% of the time. Django is a very homogeneous framework; it's easy to use, learn, deploy, maintain and has built-in ways to do just about anything you'd need to do in a web application.
Rails is more like a piece of flypaper, that you trow a bunch of stuff (gems) at and pray they stick. You can't even upload a file in Rails without using a plugin.
If you prefer Python instead of Ruby I suggest you to start with micro frameworks like Flask or Bottle to get an idea how frameworks really do their job. And don't let that "micro" word to mislead you. You can create great applications with them.
Web2py is easier and more fun to use.
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.