Id say pic the engine that has the best platform & overall condition for the price, There is no sence installing thin gaskets on the 440 because all those BBs came factory with the steel shim gaskets, You can mill the heads, but with a piston .180" in the hole won't do you much just cutting off .030", even .050" BTDT, If the 383 was rebuilt useing factory style pistons then definitly go for it, you never know, Don't ever think a 383 won't kick a 440s ass, because i've seen it done many times, & as for the 383s derability sheezz, they are by far the strongest BB mopar ever built, They are rugged & tough & will run like hell, A friend of mine had a 74 duster with a .060" 383, 12.5.1 compression, .590 cam, Victor intake, 850dp, 4.56 gears & 5200 stall, He ran that car in brackets "every" weekend for 10 yrs. & only re-ring it twice & fresh bearings, won tons of cash, kicked ass on many 440s, At 3700ft Alt, car ran 10.9s, in dallas it ran 10.4s, In bay town it ran 10.teens & it twisted the driveshaft right out of the car, he shifted right at 7000 on stock rods with good bolts, yes stock rods. I'd take an HP 383 anyday over a smogged out 440.