I would consider all the parts that you wouldn't mind changing.
If you went with a big block, you'd have to change engine mounts, bellhousing, flywheel, headers, etc.
If you went with a Windsor/Clevor, you'd have to change or modify the headers because of the taller block height.
There is absolutely nothing wrong with a Cleveland, nor with the oiling if you keep it below 7500. A 393 or 408 stroker kit in that block with a nice set of heads and a cam matched for what you're going to be doing the most would make an excellent platform...and you wouldn't have to change anything else.
Having 255 at the tires is roughly 325-350 at the flywheel which is no slouch. It would be very easy to have an extremely streetable 500hp at the flywheel, that would run on low octane gas, putz around town/cruise/parades, but blow your shorts off when you got in the gas.
I do a lot of Cleveland stuff....even started my own forum a few months back.
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