When asked if driving on the highway was too stressful for the engine in my ‘36 sedan, John Miller, my engine builder and loooooong time flathead V8 enthusiast said, “Don’t worry, just drive it.”
When asked if a Columbia or similar OD was a good idea he said, “Don’t worry, just drive it.”
When asked about oil viscosity and change intervals, valve adjustments, carburetor rebuilds and the like he said, “Don’t worry, just drive it.”
My take on all of this is that Henry’s venerable side-valve V8 is pretty much unbreakable in stock form so long as you take reasonable care of it and don’t allow it to overheat. Mine routinely sees 4,000 RPM and sounds sweet all the while. Do I ever worry about sending a rod through the block or blowing the bottom end out? No, not really. If something ever did happen out on the road I can probably fix it with a crescent wrench and some bailing wire.
I think a lot of folks are far too easy on these machines (though it is understandable if you just spend six figures and a decade’s worth of time restoring a 1,000-point car); they were designed to give years of trouble-free service under the most trying conditions. My 59L block was already hogged out 0.060 when I got it and John took it another 0.020, so it's probably been rebuilt, what, at least four times? Like him, I say, “Just drive ‘em.”