Howdy Jake:
I've forgotten what trans you now have behind your '61(?) 144.
Know that the C4 is heavier than either the 2.77 three speed or the 2 speed auto that came behind the 144. The extra gear of the C4 would be a big help, BUT- the 144 block was not drilled and tapped for the C4, so getting it to fit/bolted up would be a major fabrications job.
The 8" rear would be considrably heavier than your 6.75" or 7.25" rear end. Both of these are Salisbury type differentials, like the modern 8.8" and 7.5" Ford rears. The 8" is a hotchkiss type differential. I seem to recall tht the Salisbury type rears had less parasitic lose than the Hotchkiss rears. I'd only recommend this change if your HP were going to the 150 and up range or if your stock rearend was giving you problems.
That's my two cents, for what it's worth.
Adios, David