
Provides information on successfully designing a Web site using XHTML and Cascading Style Sheets.
https://www.abeautifulsite.net/posts/bulletproof-components/
Randomizing content is a great technique to test for this.
As for web typography, you want to check of the latest generation of font embedding because that's where the real magic's at. The most known web font solutions are: CSS3 (font-face), typeface.js, cufon, flir, sifr, Google Font API, Typekit.
Here's a list of quality books on design and typography:
A History of Graphic Design
Before & After Page Design
Designing Brand Identity
Emotional Design: Why We Love (or Hate) Everyday Things
Graphic Design Solutions
How Designers Think
Information Dashboard Design: The Effective Visual Communication of Data
Making and Breaking the Grid: A Graphic Design Layout Workshop
The Complete Manual of Typography
The Designer's Guide to Color Combinations
The Elements of Graphic Design: Space, Unity, Page Architecture, and Type
The Elements of Typographic Style
The New Typography
The Visual Display of Quantitative Information
Thinking with Type: A Primer for Designers
Typography Workbook: A Real-World Guide to Using Type in Graphic Design
Books on web design: About Face 3: The Essentials of Interaction Design
Ambient Findability: What We Find Changes Who We Become
Bulletproof Web Design
Cascading Style Sheets: The Definitive Guide
Designing Web Usability
Designing With Web Standards
Designing the Obvious: A Common Sense Approach to Web Application Design
Designing the User Interface: Strategies for Effective Human-Computer Interaction
Don't Make Me Think: A Common Sense Approach to Web Usability
Homepage Usability: 50 Websites Deconstructed
Information Architecture for the World Wide Web: Designing Large-Scale Web Sites
Information Architecture: Blueprints for the Web
Interaction Design: Beyond Human-Computer Interaction
Rocket Surgery Made Easy: The Do-It-Yourself Guide to Finding and Fixing Usability Problems
The Essential Guide to User Interface Design
The Inmates Are Running the Asylum
Thoughtful Interaction Design: A Design Perspective on Information Technology
Web Form Design: Filling in the BlanksYour wish list is all over the place. It would help to pick one of the goals listed (i.e. Ruby, or Node, or Python) and hone in on that. Once you figure out what language you want to learn, devour everything on the topic from these sources: * Peepcode tutorials * Slideshare slideshows * Youtube videos or other longform tutorials
Get a Hello World example running in your new language, and then see if you can get it wired up to a database. Congrats, now you're up and running...
It's not sexy or new, but the book the Pragmatic Programmer is the bible on how to become a good programmer and not just a hack.
RE: How to build a web app - read Getting Real by 37signals, this will give you a nice high level approach. This is also a great introduction to agile development principles.
"but I never really have an itch to scratch" sounds like you're not brainstorming hard enough. Even in your post there's the seeds of many different itches. Find the most basic thing you trip over every day, and write a tiny tiny software tool to fix that problem.
Last but not least, sounds like you could use some more experience with front-end concepts. I recommend Bulletproof Web Design by Dan Cederholm as a great overview.
Technology moves too fast for anybody to keep up, just do your best and always keep learning! Good luck