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Well first make sure you have the correct dipstick length and tube length for a big block 727.
Then make sure you haven't overfilled the pan capacity.
Third, replace the O ring anyway, but clean the dipstick tube and the tube well in the trans, with solvent so it makes a nice non slippery fluid...
I believe you can because your not changing the engine deck height, or camshaft... its just a head swap.
If all the bolt holes for intake, block, exhaust manifolds, are the same ... should be no problem
That's my two cents. FWIW.. :)
HR20