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The pistons in those 500" kits are like an inch tall. I can't imagine that has any benefit aside from bob weight. there's almost nothing to prevent piston slap, it's a weaker piston, there's higher side-loading.
Since my application is a street engine, w/ pump gas, I want to build for longevity. Hard to give up 30 cubes though.

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I totally agree & on the 30 cubes me & a friend are soon going to start on a 535 cube RB (4.5" stroke) with a 440 source kit/super stealth heads . I told him lets go as big as we can as nobody that I have ever spoken with (or heard about) has built an engine & lamented later on after the fact that they just had too much power to deal with & didn't know what to do with it