Jeff
One big difference between a vintage car and a vintage watch. The performance, and especially the reliability, of the vintage car is generally surpassed by the modern reissue. This becomes an issue when you're sitting on a narrow shoulder of the highway on a dark rainy night with a broken alternator.
For the most part, modern watches don't perform better than their vintage ancestors, and the downside of a watch that gives up the ghost is much smaller.
The other reason for buying a reissue is because the originals are simply too rare/fragile/expensive for daily use. This is the case in the guitar world where instruments that not long ago were just beat up old guitars, are now commanding prices close to six figures and beyond.
When a 1938 Martin D-28 or your 1956 Strat is worth $100K, a $3,000 reissue of the same guitar makes some sense.
It seems to me that this isn't the case with watches in general, and Heuers specifically.
A vintage Carrera or Autavia isn't that much more expensive than some of the reissues, and the vintage watch is likely to hold its value better. When you're talking about something like a Monaco, the equation changes, at least a little.

best
Allen