No way. The manga portrays their connection through mutual respect and competition in their journey to become great heroes. A kiss is not part of that narrative at all.
I think it's a toss-up. Deku has potential and is constantly evolving, but Naruto's strength and strategic thinking give him an edge. It could come down to the specific circumstances of the fight.
It's hard to say for sure. Deku has grown a lot, but All For One is a powerful villain. It depends on various factors like their current abilities and the circumstances of the battle.