Opinions on 360 vs 440

Good Morning all, so I was B’s deep in my 74 Dart Swinger, planning on a 440 swap…along came a sweet 69 Swinger with a 360 that I bought and now selling the 74.

I bought a 440 builder, tore it down and had it bored .030 over, cam/crank tunnels aligned, new cam bearings, completely balanced, have new pistons, the a body oil pan kit, Schumacher headers, cam.

But the 360 is in there, I do need to get the correct flex plate as there is a bit of a vibration, and it’s a tired motor.

Now I’m not sure if I want to:

Just refresh the 360 with new gaskets, bearings, rings, new cam. And possibly do a torqstorm supercharger down the road.

Go 408 stroker.

Or just do the 440.

I’d love the 440 but now I’m concerned with how much of a bit*h it would be to work on after already working on the 360 a bit.

It’s just a street car to cruise/ haul a** around in.

Just curious on opinions or those who have been in the same shoes?

Also, I wouldn’t be selling the 440, I would keep it and one day find a W-150 or maybe even B body to toss it in.
Power is for speed.
it takes power to push wind, so if you are a dragracer, you have that basic target to achieve; and more to get there quicker.
But for your stated purpose, a street car is limited somewhat to being a two-gear car that tops out at around 65 mph.
Furthermore, your Swinger, unless you perform some sheetmetal surgery, is limited to about 255/60-15 tires..... which a stout 318 can annihilate in first gear, at least. Therefore;
IMO, you can just build to a modest powerlevel at a modest stall.

The 360 is already overkill to 255s; but what you can do with a stout 360 is gear it up to cruise at a lower rpm , which affords a lower rear gear, than a 318 would need for the same/similar amount of tire-frying/haulingazz. Ima guessing one>two sizes smaller; so similarly built, whatever a 318 can do with 3.91s, a 360 can do with 3.55s, and with careful aforethought, maybe even with 3.23s. This opens the door to a more comfortable hiway cruising experience.
This continues with a BB, but the economy factor cannot keep up with lowering cruise-rpm because of the difficulties of maintaining engine efficiency as the rpm falls. and as said 255s negate the BB edge entirely.
However, if you modify your Swinger to not spin forever, well then all bets are off. And even the 360 is gonna need help in the traction department; 255s are just not gonna cut it at WOT.

All your Swinger really needs, is to install a stout Big-Bore 318 or a 340/5-speed stick, and gear it to redline in Second gear, at or near 60 mph. This would haul plenty of azz . If you solve the traction issue, then a 360 would be gravy, and you can trade the 5-speed for a Four, and regear again.

These are my opinions, based on my experience with the SBM.
As a streeter, I have never wanted more than a small-block. My modest but high-compression, 367 goes 93 in the Eighth, at 3457 pounds with me in it, and with 3.55s; so what streeter needs more? This is not a brag, rather a reference point, and possibly the upper edge target of azzhauling. IMO, it is waaaay overkill, lol.

Well I should also add that my experience began with 111"wb cars back in 1970, and they are a beotch to keep straight with skinny back tires spinning. Well not so much straight as, when they get off-line, they tend to wag their tails, which can get ugly in a hurry, and my Swingers all did it. Which is why I switched to the big-tubbed 108wb cars, and specifically the fastback Barracuda which carries some extra weight just about right over the rear axle. My cars spend a lot less time in the bodyshop now. Well to tell the truth, none of my 108s have I crashed.... lol.

I got no dog in this hunt so whatever you do, is cool.