Out of all of them...based on teams, perhaps maybe Clair gave me a tiny bit of trouble..But not much. All of the trainers I beat on my first try..Perhaps because I overleveled my starter? Anywho, Clair was annoying..Making me go in the Dragons Den to get me a stupid badge! Argghhh. Another one is Blue..=.=". He made me go all the way to Cinnabar Island, and then he HAS THE AUDACITY TO TELL ME TO GO ALL THE WAY BACK TO VIRIDIAN CITY?!?!?! And the first time I met him I didnt have all the badges yet! So I had to go to the Seafoam islands, AND THEN beat up Blaine, then go ALL THE WAY back to Cinnabar, and THEN he makes me fly all the way to Viridian to fight him. He has some...*blank* =.=". His team was a bit harder than Clairs, though I eventually mopped the floor with it.
About personalities, definitely Blue and Misty and Clair. Clairs attitude is just way to like a little girl who doesnt get what she wants. Misty seemed to be mad at me for breaking up her date~, and Blue was just way too arrogant..That is, until I beat him up.
If Red could also classify, I would say he annoys me to no end. I finally get the nerve to fight him, and when we start battling he doesnt talk?!?!? What a noob XD.