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I too did WE+TA last year. I live near SF and thus started there, July 18 to August 23, 37 days. I had ~17lbs on a seatpost rack (including backpacker camping gear), plus a hydration pack (a few pounds with contents, not including up to 200oz water). I was two panniers lighter than any other touring cyclist I saw, which surprised me (expected to be light, didn't expect that much)
My schedule forced me to travel at high summer and be done by August 24. It was definitely hot. The Silver Springs, NV casino marquee said 95°F when I stopped for lunch, and another customer mentioned 103°F as I left. But the aridity made it a very bearable heat in cycling shorts, a jersey, and Pearl Izumi "sun sleeves" (purported to make perspiration more efficient). I say that even tho I'm not morning-person enough to be capable of starting early to avoid the worst heat: every day Dayton to Cedar City ended early evening after biking through the worst of the afternoon. If you're weather-resistant, July and August are totally feasible. And if you can wake up early, I don't even think that's a requirement. I'd actually say high summer was an advantage in letting me have just two sets of clothes, with polyester long-sleeve town shirt the warmest thing I had. I'd probably have carried more in spring or fall.
I had few headwinds that I remember. The only bad ones were Baker to Milford, UT and a horribly stiff bit from Larned to Seward, KS. As far as good tail winds, I got some for the straightaway ~30mi before Eureka, NV and for the day into Pittsburg, KS. I talked to one person who said either way was a crapshoot; my bet is west-east is typically better but the difference isn't huge, and it's easy to get unlucky anyway.
I used sleeping bag/pad/tent around half the time. I had about seven nights where I had to camp and couldn't stay in a motel. (I never considered Warm Showers, felt I couldn't give advance notice enough to be polite.) But most of those you could work around by biking further or planning better. If you want to not camp at all, it's possible, but you'll probably have to sacrifice to do it (and reserve somewhat in advance in Nevada).
Regarding pace. 100mi/day is doable. (Although, I didn't aim for it out west, did a comfortable ~93/day average, planning to recoup miles in the east.) But no days off, or 110-120/day to "buy" a few, really wears. I enjoyed my trip with no zeroes because I have high tolerance for the mental stress and was at the age/shape to pull it off. But any extra time for a zero, or even less-ridiculous days a few more times, would have made it a lot better. As for my regrets because of that, I count Monticello (in Virginia) the strongest. (I've been to Zion and Bryce before.)
For comparison, my burn rate was ~$105/day not including transportation to/from the trip. I ate in restaurants fairly often and never tried to minimize spending, so those numbers could be cut easily if it mattered (although I'd start by camping more, if it did).
zzzz's point about speed is spot on. I returned to around-town cycling a couple miles an hour slower on average, probably from semi-sprinting most of the time around home and almost never pushing myself in those 37 days.
