Opinions on 360 vs 440
I like when people build a 400+ cid small block and act like it's still a small block and somehow they won with an underdog, yes technically you got a physical sbm but if we're comparing engines with heads that have similar power potential eg.. 600 hp what's the difference 340 vs 440 vs 543 vs 416 they're all gonna be capable of 600 hp just at different rpms.
But for the OP building a streetable say .9 to 1.2 hp per cid
360 = 325 to 430 hp
445 = 400 to 535 hp
And a refreshed 360 ain't gonna be making over 400 hp
The OP dealing with what he's got now not some imaginary 408 build, plus why spend money on a sbm stroker kit when he could put that money towards a great top end for his already rebuilt 440 short block.