I'd go with the Windsor, man.
Reasoning:
Reasons you already mentioned
-The SBC requires you to modify your trans tunnel.
-The SBC is quite a bit heavier than the SBF (~150lbs).
-SBC parts aren't as ubiquitous or interchangeable as SBC fans would have you believe.
-You have to hunt for a front sump oil pan for the SBC. SBF has that stock.
-the excellent autolite/motorcraft 2100 are a tried and true setup on SBF. It doesn't get any more simple/reliable than that for carbs. There's also the OEM/Holley 4bbl carb that you can get for dirt cheap if you know where to look. It's the same thing as much more expensive 4150/60 Holley part.
-no core shift problems like on SBC.
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