Cyl sidewall wear with a 416

Also when putting more stroke in the engine the rod/stroke ratio is affected and sometimes this puts alot more pressure on the cylinder walls than if were stock. The rod is actually forcing the piston into the side of the cylinder causing the early wear. Replacing stock length rods with longer rods help but then you have to go with custom pistons with a different pin heighth to move the pin closer to the top of the piston.
I've heard that if you have bored the block out quite a bit and put a stroker crank in you can actually push the piston right through the side of the cylinder, prob at high rpms though.

Not sometimes but ALL the time.

The factory was not wasting time and money by having a big block with a higher deck for a longer stroke. They did it so the pistons could have a longer skirt and the engine would last a nice long time even under hard use and 3.75 inch stroke

In the 70's for circle track racing Mopar sold a crank that gave the 340's , 3.55 CI, I forgot the ex spec, think it was a 3.58 stroke crankshaft. Heck that isn't even close to 4 inches. Its now 35 years later but are engine parts or motor oil that much better today ? Maybe machining is and there are proven 4 inch strokers out there, still seems like too much stroke for my taste. Why stink money it to something that might not withstand much abuse--why not just get a stock stroke BBM-be cheaper and last longer--yeah takes up too much space in the engine bay--only negative about the big blocks