Sorry you didn't get an answer. Unfortunately, as with many things, the answer is, "be someone who already knows all the things that you're trying to learn", o

Sorry you didn't get an answer. Unfortunately, as with many things, the answer is, "be someone who already knows all the things that you're trying to learn", or, "be an old person who witnessed the progression in real time". You could try replicating the old person experience by starting with something like Dave Raggett's introduction to HTML or anything that focuses on HTML 4, and then look at why HTML5 added the things that it did. alistapart.com also hosts a lot of articles on this type of thing.