I too, with another male friend, will attempt the w to e Southern tier, starting in October.
We also do photos and electronic notes. Rather than fussing with maintaining a website or keeping an on-line diary, I have always just kept my notes and photos with me and done periodic email updates to the friends at home. Once home I upload my things and then work on them until I am happy with them. In the last six years I have done eight trips in this way, most of them 2-3 months.
This said, however, I am continually looking at the possibility of keeping my things on-line as I go. The crazyguys site looks great, but half of my trips are trekking and climbing rather than biking so that would let me out there. The other problem I have is that the resolution that I like in my digital photos results in 1.5 to 2 megs per photo, which I think is too large to upload to these sorts of services.
We might see you on the road.