Short stroke motors (oversquare) are more reliable for daily use. Long stroke motors (undersquare) make a lot of torque, but really limit RPMs. With the OHV engines of the era, higher displacement was better achieved by increasing bore. Stroking a motor takes a lot of engineering to function the same way. Boring a motor (within reasonable limits) was as simple as re-honing the cylinder walls to accommodate a larger piston. Also remember, in an OHV engine a higher revving motor would still be under 6k (under 5k was far more common) most of the time. Nearly all American engines of the era were OHV, with only a handful of exceptions. The Chevrolet SB 302 was a destroked SB 327 using a crankshaft from a SB 283. This gave it a bore of 4" and stroke of 3" for a ratio of 1.33! Not surprisingly, it was used for SCCA Trans Am racing and was quite capable of reaching 7000 RPM, while producing 350+ hp on a dyno. Not bad for a street engine measuring less than 5.0L. Keep in mind, this was being used in a car weighing less than 3500 pounds.
Short-version: There are advantages and disadvantages to every engine configuration you can come up with.