Stock '69 318, t-quad vs q-jet vs holley vs edelbrock?

I recommend,
both a higher stall, AND gears in the range of 3.91s plus/minus one gear size, plus the Limited Slip and big-boy tires.
I like a good rowdy Dirt-Jerker2800 TC.
When you do the gears, you will need a new speed-o gear.
When you do the hi-stall, you might as well install a shift kit; and because I can, I would also rebuild the trans.
When you install the 4bbl, you will want to upgrade the trans anyway, and this will want a new governor arrangement; and she will want a free-flowing dual exhaust.

(edited for brevity)
while this is all spot on, i think it misses the mark.

if you have a smooth grand to spend and a 318 2bbl that money is better spent on a 4bbl set up, EI and a cam.

is it going to be optimal with a clapped out slush box and some long legs out back, no.

but a torque converter, shift kit and gears is gonna set you back at least a grand and you'll still have a wheeze box 318 2bbl

are those worthwhile and important upgrades, yes. but this is kind of a forest for the trees here. immediate gratification is a 4bbl

however, if you don't have discs up front do that first.