I play vintage equipment a few weeks out of the year as a change of pace. I have kept every set that had extended runs in my bag over the years and my preferred vintage set includes black-face MacGregor MT's (saddle-back) 4-9 with an 11-wedge (I have the 2 and 3 but don't carry them), 1950's era Walter Hagen 2-wood with a driver shaft that I in it back in 1982 or so, Toney Penna persimmon 5-wood, and a Ram TW-55 sand wedge. Last time out I putted with an aluminum shafted Wilson 8813, sometimes I'll use a brass Spalding Cash-In. I found that last-year's 3-piece Kirkland worked very well with this set, too much spin for the modern equipment, but just about right for the older stuff.
I agree that the game is a little more challenging and interesting with the old equipment. If I committed fully to them I think my scores would be fairly similar even if how I got there looked different.