I support better heads, cam, headers, lower gears and the 518 overdrive transmission for the 360 for a daily driver and it could run very impressive for what little you invest... Most important key words here... "Daily Driver"
It seems you were leaning a little more towards the 440 which will run really well and likey more than you need.... Again for... a daily driver.
The stroker is even further down the road for a daily driver. All the things on your anti stroker list are not "myth", but they fail to explain why.
Do some research on rod ratios and their affect on piston skirts and cylinder walls for wear. The 360 has the worst rod ratio of any of our old Mopar V8s to start off. The other thing that is key to why you have people complaining about breaking rings and damaging cylinder walls is because of the short piston skirts that are the product of any stroker. A long stroke with a shorter deck height is where you run into potential problems. The piston has to get short and thus will wear more and is not as stable in the cylinder and it gets worse with the extra clearance that better forged pistons require.
For an occasional use weekend street car to eat up the competition, great, I have one RB 493 and 2 stroker Hemis but they will not be collecting a lot of miles and a 4.15" stroke in an RB block with a 10.72" deck is still pretty well proportioned. I was going to stroke my 360 for my boat to a 408, but when I saw how short the piston skirts got and that the oil ring went accross the wrist pin, I changed my mind, as the boat is going to be hard enough on the engine in the first place, and I plan on keeping it long term and using it as much as possible, so longevity made me stay with the stock stroke and a big block was too heavy, so I think the 360 was the best choice.
Here is the difference between piston heights on a 572 (left) and a 528 (right) in a 4.5" bore Hemi Mega block. The 572 ends up with a very short skirt, but as I say, it will not be driven very often. I like short skirts on chicks, but not on pistons.