While touring, (I have done both supported and unsupported), it's inevitable that I strike up a conversation with someone who says he has wanted to tour but never got around to it. Most times they talk about a solo epic tour and just thinking about all the things that could go wrong stops them from taking the plunge. My answer has always been for a first tour at our age, "plan a tour, pick a support company, and go".
I have been talking about riding the GAP since 2009. This year neither of my regular partners is able to tour, and ironically this is the year I'm riding the GAP. I signed with Rails to Trail group who do an annual Sojourn which this year is the GAP. The price is right and I was able to mix camping and B&B/hotel accommodations.
If you have been thinking about touring for years, why not this year. Look into different touring groups and sign up soon. The good ones sell out very quickly.