What I've learned from playing highly-ranked golf courses is that the majority of them are overrated, and that there are legions of $50 golf courses that are twice as good as many $250+ courses.
Okay, let's have five examples of overrated $250 courses, and give $50 courses that are twice as good. [I don't think I could come up with five of the latter, myself.]
Tom--
"Highly-ranked" being a relative term (and cost being tied to public perception of a course regardless of its actual quality), here are some pairings I would propose. In each case, I would rather play the relatively inexpensive first course than the second to the tune of at least a 7-3 10-round split, and the second course generally costs significant multiples more to play than the first.
I'll freely admit my splits are partly in consideration of the relative value props (i.e. not a 100% straight architecture comp, although some of them are, like my CA, CT, NY and SC examples) but I feel compelled to represent the overwhelming majority of golfers who don't have the means to play high-$ courses often or at all.
AZ: Papago > Wigwam Gold
CA: San Vicente > The Grand GC
CT: Keney Park > Lake of Isles (North)
FL: Brooksville CC > Innisbrook (Island)
FL: Riviera Ormond Beach > TPC Sawgrass (Valley)
ID: Circling Raven > Coeur d'Alene Resort
MI: Diamond Springs > Boyne Highlands (Hills)
MI: Grand Beach > Harbor Shores
NY: Copake or Orchard Creek > Pound Ridge
SC: Charleston Muni > Kiawah Island (Turtle Point)
WA: Liberty Lake > Salish Cliffs
There's 12 examples, though a few of them stretch the criteria a bit (i.e. Circling Raven is more a $100 course but compared to the $300 CdA course it's a no-brainer).