At 66 I'm considering a tour for the first time in over 40 years. And I never did that tour either. I am looking into the NYS Empire Trail as a first tour, and the considerations there are: Ease, the terrain is particularly flat, Hotels nearby since I'm not camping, Restaurants too, Family stops along the way, civilization, ease of transport, starts in my college town (Buffalo), finishes 5 miles from home (NYC) and a high portion is off roads (but not off-road). It helps too that I can interrupt the ride at a few points, get on a plane or train to go home, and then go back to finish the ride. I'm not planning to do this but just knowing it is possible removes some worry, plus allows my wife to ride any section of it with me without a huge commitment. Her brother lives at the 1/3rd mark and I have cousins at the 2/3rd mark, her mother lives at about the 3/4 mark, and we have friends that live on Lake George. Lake George is the opposite direction of the trail from Albany and if we went that way we'd end the ride there.
I was on a driving trip through the west about 10 years ago and I remember commenting that I couldn't understand how anybody crossed through here on a bike, say across Eastern Oregon/Nevada/Utah. Way too much open road with no refill stops. I guess you plan around the stops you need to make.