Well as for the last part of your question and taking longer periods of time to tour - It's really simple, I think. Do you want to tour or work more? At least for me, it's not a mystical secret that I've figured out that the rest of the US hasn't. I've just decided that I'd rather put my job on hold for a few months each year or two and go experience some of this world. That experience is worth more than the money to me. But I don't own a brand new car or a big house, and I'm not wrapped up in the typical US life of the latest reality TV shows and having the latest gadgets/fashion, etc. I lead a simple life within my earning limits and enjoy hiking and bike touring. If you want to go ride down the West coast(which shouldn't take you months, so I think you should go for it and I think you'd love it), make that a priority. I'll warn you, though, you might get hooked and end up having to find a new job that you can take off for months at a time once in a while.

As for working from the road, that is something others can hopefully help with. It would, perhaps, be a wonderful situation and let you "have your cake and eat it too" to some extent, but I think it's definitely a rarity. Personally, I don't think a tour would really be the kind of tour I want if I were worried about work all the time, but great for you if you can balance it out.