Are you trying to edit the ruby files while the ruby application is running?
Or are you using the python scripts to generate a project, like cookiecutter?
Ruby does support reflection and metaprogramming so you can:
check if a method exists using respond_to?
define a method using define_method.
If it were me, I'd do everything in ruby, but it depends ...
Sounds like you should have a look at Drupal (a CMS).
If you would combine it with contributed modules such as Views, Group and Feeds you have most of the features you're looking for. From then on it would only be a matter of configuring it all to make it a perfect fit for your needs.
There's a few things you could try. There is a New Relic app for monitoring rails. You could try skyligh.io also (I have found a lot of people moving from new relic to skylight). There's also a way to tail your log files with capistrano (http://www.talkingquickly.co.uk/2013/12/tailing-log-files-with-capistrano-3/) or if you feel in the need of hard work, ...
This is my experience, coming from Eclipse.
If you want a full featured IDE pay for Rubymine (they have a discount for many things).
If you want a zen code experience go for Github Atom.
As I said I first started from a Java background, and by default I used to program in Eclipse. It was awful already at the time but that was my only ...