OK, here is my plan, see how it meshes with yours...
Quit my job, selling the house, should close mid August. As soon as the house closes I will be bumming around the western US in my pickup camper, towing a trailer with my KLR 650 and my bicycles. (I know, that's cheating). I will be doing a bicycle tour from Bozeman MT to Portland OR, then working my way south to San Antonio TX, where I have friends. Planning on leaving the truck and trailer with friends in San Antonio, and doing the HU travellers meeting in Copper Canyon, and heading south from there, although I am toying with the idea of running the San Antonio marathon the 2nd weekend of November.If I am by myself I will probably turn around in Panama and head back north. Under the right circumstances, I might be convinced to go to South America, though.
I have taken a couple of motorcycle trips into Mexico, and speak a few words of Spanish, so I am not a total rookie, but am not a global traveller (yet!). One of the things I would like to do on the trip is spend a week or 2 learning Spanish. I found on my last trip that I would have got a lot more out of it if I could have communicated better with the locals.
Let me know your thoughts.