Tom,
You won't get much argument about some courses being better then vs. now. However, the real question (and the most subjective one) is "When do you think they were at their pinnacle?"
At Cherry Hills for example, our Master plan is based around a date of 1937/38 which was at the time of the club’s hosting of the 1938 U.S. Open. From all the old photos, aerials, drawings, etc. that we had/discovered, we believe the course was at it’s own pinnacle around that time. We know Flynn was contacted about recommended changes to the course (mostly tee work) which was done prior to the tournament though we have no records that he ever returned to the course after it was first built. Soon after the Open, we believe the design started a downward spiral of changes and these changes are well documented in our plans.
Was this the course's pinnacle, who knows for sure? We do believe the course held up well through the depression and we felt this was the timeframe to aim for.
I will add that one thing we know for certain is that the course in 1938 was far superior to what is there now. At least that is my opinion.