The good thing about using what you already have as a base is that everything fits and you won't be hit with tons of hidden costs. Changing motors means changing exhaust, pulleys, brackets, mounts, fuel delivery (for an LS), etc.
Maybe consider aluminum open chamber heads with a compression of 10.5 - I have 10.6 and run 93 octane no problem. You need to get the part number of the pistons, with the cc of the dome, and plug it into the compression calculator and see what your C/R is with a 116 or 119 cc head.
Open chamber heads, a dual plane intake, 750 carb, 2200 converter, and a 3.23 gear would be a cost effective solution. That mechanical cam would need to be toned down, too. A more street friendly hydraulic would fit the bill.You would still be able to roast the tires at will.
Or, keep the rear gear (what is it?) and the TH400, but add a gear venders overdrive. Not cheap, but you will save the cost of a gear swap.
You may have better luck selling your stuff while its on the car in running condition.
Good Luck!
Mike