For a web designer that works with css, html, and php, the only thing keeping me away is deployability. It seems that without learning git and the ways of my terminal, I have no way to make a web app with RoR. Not that I don't want to learn. I do, badly. But I just wish the barrier to entry could be lower. Either that or I just need to find a better tutorial going from nothing to a very simple app on Heroku and showing me how to experiment with it.
Having done both PHP Zend Framework deployments, which require mod_rewrite rules in each vhost, and Passenger deployments, which only require touching a text file to do restarts, I much prefer Passenger deploys.
You don't need Git to use RoR ... but try and learn it. It's awesome ;)
Git also comes with a SVN bridge, which works wonderfully for me.
Also ... Rails has its own development web-server. You don't need to have a production environment to learn it.
And I really recommend that when learning about any web framework, in any language ... just learn how to deploy a production server by yourself. It saves a lot of pain later on ;)
Not to mention that I wouldn't use Heroku ... sure they provide a valuable service, but personally I get a cheaper deal by getting EC2 instances and configuring them myself. It's hard the first time, but then you can scale your infrastructure easily ... EC2 is wonderful in that regard.
Do you have any guidance or suggestions for reading material for how to migrate from using Heroku to going directly to EC2, for someone who is somewhat new to sysadmin?
I would recommend you skip rails and go for Sinatra. I found that rails had too much for me to learn to find it useful, a bit overwhelmed by the convention V's configuration thing. That is the rails convention didn't really match my own.
Sinatra doesn't have all that.
A combination of Heroku, Sinatra, and DataMapper (nice, cleaner, simpler alternative to active record) and what you have is a very easy to deploy application.
I'm doing the above, and doing it on Windows (sorry, I'd love to use Linux but my wife uses this machine when I'm not and has some apps that are not replaceable, and I don't want to mess around with dual booting. So when I get FU money I'll be Linux all the way).
I second the Sinatra recommendation. When I tried rails for the first time, it felt very large and unwelcoming, with a bunch of files that I didn't create sitting in my directory hierarchy doing unknowable things. Sinatra behaves just like any other library and requires far less of a time investment to pick up and start using.
go through the articles slicehost has written up to get rails and passenger installed and your app deployed. They are fantastic and you'll be very comfortable doing it anywhere else afterwards. http://articles.slicehost.com/rails