Hmmmmmm.....
Well, it's all too easy to make year one Pebble Beach area and say Cypress, Pebble, MPCC. I just figured that while sure, there is a lot of benevolence here, one ought not to COUNT on it... and since we are talking "modest means" we also ought not to include big-ticket items like Pebble.
Tony's sub-clause also would change things considerably. I seriously think that means two different lists - or at least some years, it's family time, some years, it's solo golf. For example one of these years Nebraska is going to feature, and well... no offense to my friends out there, but that's not an area the wife and kids would pick for vacation.
So, let's change this a bit.
Year one: SoCal. Fly into LAX, use connections to play one or another of LACC/Riviera/Bel-Air. Then play at least two rounds at Rustic Canyon. The former will give you traditional golf at its finest, the latter will allow you to see a modern version of the same, and will save the pocketbook. Bring the family - countless things for them to do.
Year Two: Norcal. Fly into San Jose, drive south to Monterey. Use connections to play MPCC, both courses if possible. If you REALLY have connections, add Cypress Point. One way or the other, play Pacific Grove Muni as well, then head north, play Pasatiempo. If you can't go home smiling after this, you have no soul. Again, lots for family to do, bring them along.
Year Three: Colorado. Fly into Denver, play Cherry Hills if you can swing it, or any of a number of other great clubs close in to Denver - Denver CC would be a great sub as well. The head east, two hour drive, play Ballyneal at least 2-3 times. If time allows, find one of the great Engh courses and add that in. Bring family, lots of hiking plus Denver is a great city, lots to see both urban and rural.
Year Four - Bandon. Enough said. This will be a splurge, but it will be absolutely worth it. Fly into Portland, connect to North Bend. Stay on-site. Play as much as your legs and wallet will allow, over all three courses (or a 4th if it exists by then) and Sheep Ranch (if that still exists). Leave family at home - go with golf buddies.
That's enough for now... I was going to head further east, but man there's still a lot West of the Mississippi to conquer...
TH