First, you can benefit by doing some RoR work, learning a new language. However, I do not know if this will be completely useful for you right now, since you are still learning. At the moment, I stick with Python and Django (or AppEngine) until you understand some of the more advanced concepts. Then, by all means, learning new languages will be fantastic.
Regarding the transition to Django from AppEngine. It's not that much. The way you define models is similar, but has different types to define. As you mentioned, hosting is another consideration.
There should be many hosting options (mod_wsgi is what you need) based on Apache. Django, in particular, is quite popular, and hosting usually extends to popular frameworks.
I do not think you need to know too much information about sysadmin. It all depends on the type of hosting you can find. The same goes for the database. Hosting providers usually offer pre-configured databases, so you don’t have to worry too much about it.
Django, along with many other frames, provides an ORM (Object Relational Mapper) that abstracts from the need to write SQL by calling methods on objects and accessing their properties. I would advise learning a little SQL to figure this out with a minimum minimum.
Django tutorial is great! If you decide to follow the Django route, I would highly recommend working through all of this. The development server comes bundled, so you can try out your work instantly without worrying about the provider. When you have something that you want to share with the world, you can worry about hosting.
I started using Windows to develop Django, and it was pretty easy. The amount of command line work you need to do is minimal. Indeed. Not something you need to worry about, as the tutorial covers all 4 teams you need to know.
Django hosting provides links to hosting providers, although I'm not sure how updated this list is.
Getting started with Django is pretty simple. After you want to post it, there will be more work, but this may happen later. Friction is minimal. Follow the instructions, you will need to start the server, configure the database (a free kit is included) and encode the first application.