Designer eager to become Developer

A LAMP stack will be easier to deploy simply because pretty much any cheap hosting you get as a playground will support it out of the box. Rails is a little more tricky to deploy. That said, Ruby and Rails is, in my opinion, more fun than an equivalent in PHP (pure opinion though so don't let that colour your experience).

I would suggest taking one bite at a time - find the easiest deployment possible for your chosen stack (if it's rails, then deploy some test projects to heroku). Learn to program a little before trying to jump in and do the Apache setup etc. Nothing is more frustrating than wanting to see your creation on-line but you just keep hitting your head against a brick wall because you can't deploy. I'll also put in a good word for webfaction for good cheap hosting that supports rails, django, and php very nicely without you having to do a lot of server admin - perfect for a playground.

Choice of language is pretty much a matter of comfort when you're first learning. The question is, do you want to be using Ruby/Rails or PHP/Wordpress/Codeigniter/etc. If you're just learning, you're going to want to code in whatever language you choose. Just for reference, you can create backends for websites in Clojure, Java, Python, Haskell, go, JavaScript(node.js), etc as well.

I'd say use Ruby/Rails if you want to create webapps and PHP/etc if you want to create Wordpress sites. Someone more experienced than me in these languages can comment further.

Heroku.com supports Ruby and from using it with Clojure and node.js apps, I highly suggest this route even if you enjoy setting up your own servers. You can also use providers like Amazon EC2/Joyent/Rackspace and set up your own box to be either a LAMP stack or Ruby/Rails.

There is a long list of Databases to choose from these days, including: MySQL, PostgreSQL, Riak, CouchDB, MongoDB, Cassandra, etc.

Truly the answer you're looking for is "Just start somewhere". The amount of tech you can choose between is dizzying and you'll eventually get to a point where you can make your own decisions if you just keep hacking.

I'd say the stack to learn depends on what you want. Basically, the best bet for a job anywhere is knowing LAMP plus frontend (which you already can). I think rails/ruby is prolly going to be harder but if thats what you like then go for it :) As far as apache goes if you just want a job as a developer basically all you need to know is mod_rewrite aka regex, and some really basic other stuff like virtualhosts, etc that you can learn in a day. On the other hand SQL is going to be harder, learning "enough" shouldn't be a problem, but to know how to use joins,views,triggers,migrations , etc is something you should start on in tandem with your programming language. I know too many developers who don't concentrate enough on knowing/managing their data when this is always the heart of your application. As far as hosting goes, with LAMP you all you need is a nix machine somewhere, I'd suggest getting a linode (http://www.linode.com/). This also has the added bonus of great docs and you can try out and teach yourself everything on your own machine w/out crappy cpanel stuff.

Good luck!!

I would just begin to expand on your back-end skills. Since you have HTML/CSS/JQUERY under your belt. Continue to work on those, and also begin with a database (MySQL works fine), once you learn basic database-ing, then begin working on the controlling logic between the two. I would recommend PHP only because it's a quick language to learn and get busy with. This gives you a solid set of skills and a good view of the process. From there you can begin to enhance what you do with the two.

Nothing needs to be super-advanced, get down and dirty and learn quickly; more advanced work will come with time. As biscarch said 'just start somewhere'.

You have to decide what kind of developer you want to be. A hobbyist would probably go with the most out of the box stuff, so would use something like rails. You could be a specialist developer who only knows one framework and language. Or if you want to be a total pro you will want to learn all the frameworks because you are very adverse to your coworkers knowing anything you don't.