There is a certain amount of conceptual overhead which happens with Rails projects that doesn't happen with PHP. Deploying Rails apps is still an order of magnitude or more harder than doing PHP apps -- even with Passenger, which supposedly fixed deployment. There will almost certainly be more configuration in a Rails app.
On the plus side, the Rails and Ruby communities have wide and deep amounts of OSS code for you to use to accomplish typical web dev tasks. The PHP community is, ahem, well, I'm sure they're wonderful people and if you're working on Wordpress they have huge amounts of well-packaged code available for you to use to accomplish your tasks.
You don't mention if you're a programmer already. PHP is well-suited to folks with minimal programming ability. I would think doing Rails without having strong object oriented programming skills would be a recipe for disaster.
For prototyping purposes, deploying to heroku is as easy as
git push heroku master
Also, I learned Ruby as my first language... learning OO was no harder than learning other programming concepts.Look into Python and Django or Pylons.
In my opinion Python has a better culture and community. You will also be exposed to functional topics like list comprehensions and generators that you are unlikely to come across in PHP.
Don't ever try to build something in PHP that needs to be clean and clear. Messy and obscure is easy in PHP, clean and clear is hard, therefor the system will be working against you all the time.
However, you can't always avoid it. Sometimes you just can't use anything else.
RoR has as down side that it requires a lot more control over the server then PHP does. Also, you need to learn to think in RoR's MVC model. It you can, RoR will be a great assistent helping you along the way. If you can't, it will be as helpful as a bureaucrat.
It's a fairly gradual step up from static HTML/CSS, and will probably be less frustrating at the start.
For web apps, I love Drupal. Drupal is a php platform, like Rails is for Ruby. PHP was easy enough for me to be building simple Drupal modules within a year of my first install, with Very little prior experience. So, keep in mind that php is not a huge learning curve and you also have jQuery, Apache, linux, project management, etc out there, fucking up your life, ;D
Here are some impressive implementations: http://www.drupalgardens.com/ http://openatrium.com/ http://groups.drupal.org/aegir-hosting-system http://developmentseed.org/ -> Their projects are cool http://drupal.org/project/modules?filters=drupal_core%3A87... -> Modules organized by usage. Go through a few pages to see some specific use-case modules. http://2bits.com/articles/presentation-28-million-page-views... -> Drupal is NOT slow when configured properly. www.whitehouse.gov is probably pretty cool.
I recommend http://sf2010.drupal.org/conference/sessions/state-drupal for an idea of where Drupal is today.
I'm curious what other HN people think about Drupal. Would love to hear.
@jonjonjon - I'd suggest finding a quick mini-project tutorial for both languages and do them. Afterwards, see how both languages feel and judge it yourself. For Ruby on Rails, there is the Rails Tutorial by Hartl
I don't know of an equivalent for PHP.
If your web application is mostly a web site with some dynamic features sprinkled in, then PHP would be a good choice because it's easy to embed straight within the HTML. If you're building a full-fledged web app (lots of dynamic content, database-backed, user accounts, etc.) then I would choose a web framework. I don't know how PHP web frameworks compare with Ruby web frameworks since I haven't used a PHP web framework myself.