I always dreamed of coast-to-coast bike touring, it was a bucket list thing with me. But like you, the time, equipment, partners, cost, etc. seemed overwhelming so I never did any. One afternoon, while riding with a friend, we were both lamenting all the things on our bucket lists that we’d likely never achieve. Time was the biggest factor for me until I realized while talking with my friend that I could do it in sections, none longer than my annual vacation. I ordered a set of ACA Southern Tier maps and planned an ambitious first leg from San Diego to El Paso. It would take 13 days to complete.
The equipment was also intimidating, but I used my existing bike, a 30-year-old old set of panniers, and other random camping stuff which I already owned. I did buy a lightweight down sleeping bag, but I could have used my existing bag as well. I read this guy’s blog:
Ultralight bicycle touring which had lots of great tips. I followed some (like buy a scale and weight everything), and ignored others (like cutting the handle off my toothbrush). In the end, I spent very little on new equipment. Since you don’t know if you’re going to do more than one tour, borrow as much stuff as you can; you’d be amazed what your friends have in their basements and attics.
As for a traveling companion, none of my friends had any interest in bike touring (most thought I was crazy). I planned to ride alone and was OK with that as I’ve traveled extensively by myself and am very comfortable with my own company. However, the month before I left, a housemate of a good friend said he would like to join me. We did one practice ride together (with all our gear) and determined that our riding styles and personalities were compatible.
That first tour was life changing; I loved it. I’d made a few mistakes in planning (i.e. don’t plan an 80-mile first day climbing the Sierras fully loaded unless you’re fitter than I was). Seeing the country at 10 mph is amazing. The kindness and generosity of people was heartwarming. At the finish I was sad to see El Paso as I wanted to keep right on going to the Atlantic; which I did in two more sections over the next two years.
Bottom line – Just go do it! You’ll be shocked at how easy it is.