Keep it coming man, we are enjoying your story and your candor over what has been holding you back. We all feel some trepidation over long distance tours, but the experiences and the sights are worth the initial feeling of uncertainty.
Like the poster said above, what's the worst that could happen? Have to burn the bike on the side of the road for warmth and walk out?
Seriously though, keep fightin' them demons and thank you for your service.