68 Cuda 383 vs a 360

Let's be realistic:

There are plenty of factory engines running around with short compression heights that expose the oil ring to the pin boss. No big deal they use oil support rails. A 4.250" stroke crank typically uses a 1.320 compression height. A stock 200k mile ls 6.0 uses 1.342 with a much thinner metric ring pack. Short pistons are a non issue here.

Most of these street engines never see the high side of 5500-6000rpm. If they do it isnt for long and typically the engine was not loaded like a drag car. Or worse, wrung out like a SCCA road race car. My point is that engines going into hobby cars owned by middle age to retirement age drivers do not see the abuse people make them out to endure. Bottom line is most guys building stroker engines finally get them in the car and then drive around "with you wallet under the gas pedal" because you dont want to break your "yep she's a stroker all right " 10k engine before the Friday night McDonalds fonzie style cruise in. All you have to do to be on top is have cutouts and use words like roller and stroker to makemthose crying doll easter egg looking street rod guys retreat for another McRib or whatever.

In my research piston speed does not become a durability issue until you start seeing some RPM. I have a 400 based 511 going together than will see north of 8500rpm. I am more concerned about oil contro and valve train geometry than piston speed.

Rod ratio...it is what it is. Built with your goals in mind and don't sweat the egghead math too much. Leave that to the OEM`s that have to support a 100k warranty.
All good points, but you know, I think maybe the biggest one....and feel free to chime in if you disagree is the modern thinner ring packs. That right there is what kinda unlocked some "free" power by reducing the heck out of friction. Because we all know the friction of the rings against the cylinders is THE biggest source of friction in a piston engine.