Lived thru a similar set of circumstances, Geo.
For me what worked was the following:
For
Shorter Routes:
1. Picked out a desirable multi-day ride route within drive-able distance from home
(which sounds alot like what you are doing now?)
to "be accomplished," but with myself-understanding and
acceptance that the completion of said route would be over time .... however long all factors impacting me would collectively cause it to take. Each specific route sort of became a hobby in its own right, so to speak. By focusing on a specific route over time,
to my surprise, it became a lot of fun, including giving me a non-stop objective to stay in bike-ride-worthy shape.
2. Picked out 4 day ride weekends. Executed each ride when I could. Completed each route thru multiple rides when I did.
For Much
Longer Routes (e.g., coast to coast/Canada to Mexico/etc.):
1. Every few years and/or in between 'jobs,' would just head on out. Just had to do it. However, again, it was a route that was to be and was accomplished a single ride section at a time.
Btw, in further response to the specific items in your Original Post ... I had to just do it all solo/un-supported. In retrospect, solo/un-supported was overall, for me, easier for many reasons I will not elaborate on herein. Pls Private Message me should you wish to trade thoughts on the gains/losses of riding solo and riding small (2-3) group and riding larger groups. All of 'em have trade-offs .... at least that is what I have found, anyways
