up to you whether you prefer a handshaker or an auto.
i prefer the aod/4r70w or a combination of them for an auto.
if this is a dedicated rig for rocks a c6 is a solid choice for a 302 stroker for simplicity assuming your running a doubler of some sort...if your rig will be under 5 k in weight a c4 is the best with a mild 302 for most guys...
a full manual c6 or c4 or t400 are had to argue against for trailer trash....since your living in the area i hope to relocate to you can reasonably drive the roads with those 3 speeds to some insane wheeling so theres not much to lose.
the zf is pretty nice as the overdrive has advantages in most cases where the road will be used.
if i were to do a gas engine swap from scratch these days that was a v8 most likely it would be a ls type engine from a late model gm truck with a 4l85 or one of the new 6l variants with a 241/205 doubler...
unless i had a 302 laying around already.
in any case stroke the 302 or use a 351 for best results if you think you will be over 5 k in weight.
on edit..
if this is the rig and you stay reasonable in weight a solid build 302 and built c4 will be a great combination even the most die hard stick shift guys would have fun with.