This is such a cool idea. Sorry for the delay you are having, family losses are always tough to deal with. However, I am glad to hear that you are planning to continue on. I might have to do something like this when I retire (which is in 20 years).
I couldn't really tell from the summaries, have you played in Columbia, SC yet? If not, let me know when you plan on it and I can possibly drive down. I used to live there, but am in Greenville now.
Also, big shout out to @jsgolfer for coming through on the golf course in Annapolis!
You are not getting it-What is harder a 225-yard hole or a 235-yard hole? Or a 325 yard hole? Or 425? Or 525?
If they are already at 56 just playing 225-yard holes adding length only adds to their score.
Cool! Your itinerary takes in the places in SW Ireland I got to visit back in 2006, plus a lot more. Good luck with the driving; I doubt I would have the fortitude to take on some of those narrow, stone wall lined goat tracks.