You seem like you really want to change so you will probably learn fast, as for resources and material to be honest most of it is available on this site.
Also don't get too bent out of shape about being broke, I am sure for a while I was the poorest PUA in the world lol I lived off scrap food I found around the house and would go out with no money. However, in true Boy named Sue style you will learn fast, good clothes etc can be done without tbh, they are hella handy but not essential.
As for your confidence I would recommend grabbing a copy of Rules of the game (instead of buying the game), or just starting out with small things such as talking to shop workers and asking directions. Then move up to chatting to random people, just ask someone how their day is going. A way to make this easier is to get out of your usual environment, go to a town that you rarely if ever go to. Lets face it you won't see most people you game again but having the added bonus of knowing you won't even be in that town again will act as training wheels.
Finally a good way to start gaming is with little competitions with your buddies, when you are out tell them the person to get the most numbers gets bought one beer from everyone else or something. This keeps it lighthearted and fun, with an edge of competitiveness.
If you need any other ideas just ask and I'm sure me or one of the other guys will help you out
