OP,
I was / am pretty much in the same boat as you. Know i needed to move away from poker but the only thing i really had that was an advantage was some capital to invest / live off for a while. I'll give you a run down on my journey so far so you know what to expect.
Around middle of 2011 decided i wanted to learn to code, I'm an Australian living abroad and coding provided all the same flexibility poker does in terms of living arrangements / work hours etc. Did some
online tutorials at lynda and chatted with some friends who code / run web businesses for a living. They gave me the same advice alot of people are giving in this thread, you need to build something. An e-commerce site, a membership site, a custom made blog, whatever. You can't just read a book or do heaps of tutorials and know how to code. It'll help a bit but the best way is to try and build something and then use google to figure out how.
In late Sept 2011 I decided i wanted to build an ecommerce site. My mum has had craft stores in Australia for years and so I decided to build an online store and put her products in it. We decided to give it a go for 2 years and if its going ok after that time we'll keep at it, otherwise we'll give up. Worst case scenario for me is i walk away after 2 years with nothing but having learnt a TON about coding / SEO / web business etc and could work for someone else if need be.
Whatever you build will never really be finished as you'll always be changing it and updating it and adding things to it but after 4 months of coding and 2 months of taking product photos (we have over 2000 individual products) we launched.
It's been 8 months since i sat down and did <?php echo "Hello World"; ?> and from there i now have an
online craft shop. (Shameless link, i know).
Its built using php and obviously html, css, some javascript and a MySQL database. I had some really good people helping me, one who is a gun coder, he's been writing code for 10+ years and has been incredibly helpful from day one, just last night he help me setup my own server as im learning about that now, going to move away from shared hosting. The other is a good friend who has run a web business for 5+ years and knows a ton about layout, design, user experience etc.
If you can get a mentor or someone who you can ask questions to it's incredibly helpful, especially for the first 3-4 months while your learning the syntax and all the different built in functions whichever language you choose has. Once you get over what I'd call the "3 month hump" you'll be fine. I started 8 months ago, 2 months i was taking product photos and the last 2 months or so I've hardly been coding but when i do I hardly ask anyone any questions, can find most of my answers on google or can figure things out myself. That being said theres always something new to learn, from getting better at your chosen language, the learning other languages, to managing a server, to SEO, the list could go on forever.
I don't know anything about ruby or python so I can't really comment on them but php is easy enough to learn imo. Other posters who know php are advising other languages so maybe they'll be a better place to start.
Once you decide what you want to build have a look around online at different sites doing the same thing. If its ecommerce look at amazon, asos, ebay etc. Pick the things you like about those sites and then try and integrate them into your own site. For example i really liked the way asos does their product filtering (
check it out here) so i built the same thing - (
check out my version here).
SOOOOO, in answer to your questions;
1) If you can find someone you can hit up with questions that is best, after that it is google thats the best for finding answers to things. I found
http://www.w3schools.com/ to be really good. When learning stuff i often forgot how to write things properly so would quickly look up simple answers on there. Tell you the truth i still forget and have to look things up, lol, esp mysql stuff.
2) Best way to learn is to build something, until you have an idea of something to build i think it's really hard to learn.
3) One thing that i find really helpful whenever im stuck is to break things down. For example that product filtering took me 2-3 days of trying to build it and getting absolutely nowhere, then i took a day off to figure out in English exactly what it is i needed to do to make it work one baby step at a time, after that it was actually pretty easy to put together. Think of each letter of code as one piece of lego and a website as the biggest lego thing you've ever seen. To build the big thing, you have to put each small piece into place one at a time, just focus on doing that and eventually you will make the big thing. (Hope that made sense).
The hardest part isn't learning syntax, its learning how to use the syntax to make something work.
If you've got any questions feel free to pm me.