Thanks for everyone's input. I purposefully left out some details in my first post. I have only done on bike tour, an 8 day, 420 mile tour with 9 friends. Loved it but it was uneventful in terms of anyone having difficulties or really bad weather. That certainly could change on a 3 month trip. I am retired and have the time and the money to do the Transamerica route. Being locked into a schedule with 13 other people could get tough given the length of time for the entire trip. I am doing a solo bike tour from my house outside of Rochester, NY, to Pittsburg via roads and then to DC via the GAP and C&O canal trail. It will be a 13 day ride in September with about half camping and half hotels. I will likely decided on how to handle the Transamerica tour after this shorter jaunt but I am leaning towards a solo cross country ride next summer