I can only speak for Ruby - it's what I chose when I moved from PHO development several years ago. 1. I am much more productive in Ruby than I ever was in PHP

I can only speak for Ruby - it's what I chose when I moved from PHO development several years ago. 1. I am much more productive in Ruby than I ever was in PHP because the language is more consistent and testing is built in. But it takes a long time to understand Ruby so that you can be proficient. 2. it's not hard nor expensive anymore. Dreamhost hosts Rails applications just like PHP apps. Linode.com has VPS setups and scripts to get you going. Heroku is free for small apps. Worry about building something deployable first, and then tackle deployment. 3. You shouldn't switch if you can't take the short-term productivity hit. You're not going to be as productive in Ruby right off the bat because it's new. My interns all agree that the first two weeks of Ruby with me are pretty rough, (80 hours or so) but after that they take off. But it takes a lot longer to program Ruby like Ruby and not like PHP. 4. My opinion will get in the way here, and a lot of the really cool stuff isn't really for beginners. But I am so happy I have the tools I need to accomplish the crazy tasks I've gotten myself into. 5. RailsTutorial.org is a great start - the pdf is free. Also, I run RailsMentors.org - maybe you can find someone there willing to guide you. However, be prepared to come with questions and do some work. Also, find a local user group and hang out. A lot of Ruby people love to help you get started as long as you're willing to put forth the effort. Feel free to ping me with questions. bphogan on twitter. Best of luck.