While I don't think there's a magic equation to calculate exactly how much more wear each individual combination is contributing to, I will say that it seems the higher displacement/longer stroke combinations contribute the most. This is based on both the results I've seen from running and broken engines after a few miles and simply by doing the math.
Of all the 347's I've seen running around, I don't think I've ever seen one with more than 50,000-miles on it. Generally, the car ends up sold or broken, (to become someone elses problem as made apparent in this thread) or a different combination is built before any of them see any sort of mileage. I have on the other hand seen pics of ones that the owners assumed were running fine, only to find visual evidence of excessive piston skirt scuffing, and/or cylinder bores polished to a mirror finish from wear in a relativity short period of time. The angle of the rods in a stroker kit puts a LOT more stress on the cylinder walls and piston than your standard 302 does. This fact is irrefutable. How much additional stress is really going to depend on how much the rod angle is increased.
This was exactly the reason I chose my 331 over the 347. While I know it's not going to knock out 200,000-miles like a basic 302, it should be good for a good portion of that and most certainly will outlast a 347, while providing as good, if not better performance characteristics in return. That 15lbs/ft of torque I miss out on with the additional displacement is more than made up for by the "revvy" nature of a more square bore vs stroke combination and additional longevity of a less stressful engine combination.
In the end, I decided the performance vs longevity ratio of the smaller stroker was an acceptable compromise for me to live with.