Thanks Fred - I'm new to this. I'm going to use one of the organized/supported ride companies and they seem to take either the northerly route (in early summer) or the southerly route (in fall). Because of work, time is an issue for me, so think I currently favor the southern route, which TrekTravel does in 4o days. Was hoping that someone may have done both and had comments or a preference to offer.Just a few thoughts...
Everyone wants something different from a tour, so your preferences may be entirely different than mine, but bringing a support vehicle into the equation is a huge negative for me. We did the Trans America in 2007 and found that the lack of car support made for a trip where we had more of an adventure, met more other riders, and met more local folks. We were able to stay in hiker biker sites, were more likely to be invited to stay with local folks, and generally interacted more with people along the way.
Part of what the tour was about was the fact that we were riding across the country and not dependent on car/van support.
We did have a few days in Virginia where we stayed with family and friends and were picked up where we stopped for the day and dropped back there to start the next morning. It was a nice change of pace and we enjoyed the great hospitality of family and friends. That said we got the least feel for what the people and places on that part of the tour were really like. I would do it the same way again for that minor portion of the trip, but there is no way I would want to have done the whole trip that way.
BTW, I really liked the Trans America route a lot. I will probably do the Southern Tier and a Northern Tier at some point, but if I were only going to do one it would be the TA.
Personally if I was in the situation where I couldn't get enough time off, I would consider doing half one year and half the next. I met a few folks doing that when we were on the TA. In my case I just took enough time to do the whole thing in one year. That meant that I had to take some leave without pay. I was willing to quit my job if necessary, but they were supportive and said I definitely would have a job when I got back. Strangely it seemed to actually have helped my career. They must have missed me while I was gone.
Another option if you have limited time is to do the Pacific Coast north to south.