Combination change, what would i gain?

Don
The 340 in my Dart had ported Edelbrocks, 293 @ .650, hydraulic cam with 1.6 rockers, 236/242 @ .050", .592/.586" IIRC, 11.4-1, X-Cellerator intake, Q-750 with 1 5/8- 1 3/4" TTI headers, 727 with a 9.5" converter that flashed 5000. At 3240# with 4.30 gears it ran 7.24 on pump 93.

The 408 that replaced the 340 was 10.8-1, the Edelbrock heads were sent to Ryan for freshening and 2.055" intake valves, no additional port work. A Victor intake that I deep port matched, Bigs 950HP, Hedman 1 7/8" w/ 3.5" collectors, a flat solid 260/264 @ .050", .633/.628" w/ 1.6 rockers. The converter was freshened for the new engine and flashed 5200, same 8 3/4 with 4.30 gears. The engine ran on pump 93 like the 340.

At 3260# the first pass it hooked up it ran 6.82, the second pass that it hooked the 8 3/4 broke. I replaced it with a Strange S-60 with 4.10 gears and with some tuning it ran 6.57 with 1.38 60'.

IIRC your car has ladder bars? It runs hard with the 360 and I suspect it will with the stroker. I'll hazard 6.80-.90 and maybe .70's after some tuning even with the smallish cam, headers and limited head flow. I'll also guess it likes 6000 rpm or close shift points. My 408 liked 6400 best, the cam was from Hughes and Dave said it was to big for what I was doing and should like 7200 in a 408ish small block. His thought were that my heads were holding it back.
I think your third paragraph has its own thread potential. I could definitely collaborate a damn near identical story.