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Different guy here, but in OPs position almost exactly. I've got in my head that I want to ride my bike from northwest Arkansas to the Pacific Northwest via the TransAmerica Trail.
I'm thinking about getting MTB clipless for handling the mountains but have zero experience with clipless having ridden platform pedals all my life.
For the bike, if I save up and buy new I'll be looking at getting either a Long Haul Trucker or a Fuji Touring. My LBS carries Kona (which I love) and Giant, but neither of their touring models appeal to me. Giant's is a flatbar and Kona's is butt-ugly.
I'll be on a budget of $730 a month (so $24 a day), how does that sound?
Concerning gear, I plan on using my one man tent and a modular sleeping system minus the patrol bag. I'll also get a second MSS compression sack for my clothes.
I was also thinking about a earth-toned tarp to help hide my bike when stealth camping. A nice camo military surplus bivy plus the bike wrapped up in a brown tarp would feel pretty safe to me as long as I wasn't camping right on the shoulder of the road.