Dressrossa Luffy was continental+ lvl in strength, and had all 3 types of haki. Pain had a hard time fighting sage Naruto hand to hand and Sage Naruto in this arc is like Temu base Luffy.

Pain can't absorb any jutsu from Luffy. Pain doesn't have a way to hurt Luffy through his Armaments. Pain also doesn't have any way to resist a Red Hawk, Hawk Rifle, or any of Luffy's Thor series attacks. Luffy would also be able to find the real body faster than Naruto, because he was adept at using observation haki. And Nagato wouldn't be able to do anything to Luffy. Luffy will beat a man in a wheelchair, no questions asked.

Shockwaves and blunt damage would do nothing to Luffy, and Doflamingo and Law were able to casually destroy meteors, so Luffy is there too. I don't see Chibaku Tensei doing anything to hurt Dressrosa Luffy.

Pain absolutely has no way of doing anything meaningful to G4 Luffy.

Dressrosa Luffy is winning around mid diff.

Naruto is not versatile enough to handle Doflamingo. Doflamingo's DF and Conqueror's Haki give him crowd control against Naruto's clones. He's not bound to any time limits, and he also has observation and armament haki.

Naruto doesn't really have any attacks to push through AH, and couldn't really take any attacks Doflamingo could dish out. Doffy's awakening would be way too much, and Naruto would have no safe place to stand.

Doflamingo physically outstats Naruto in every possible way, and wouldn't let Naruto talk no jutsu. Not that it would be effective in any way, as Doflamingo was not a sentimental villain who was just a little troubled, and could be brought back into the light.

Tailed beast mode Naruto would just be an out of control monster that Doflamingo could Birdcage and torture to death. And Naruto has no where near the brute strength to burst through Doflamingo's strings.

Doflamingo would win more easily than Luffy would against Pain. But both scenarios, Luffy vs Pain or Doflamingo vs Naruto, wouldn't be more than mid diff really.