I have two questions. 1) Where do you get the itemfinder?

1) One of Professor Oak's aides gives it to you after you have I think 30 Pok�mon captured in your Pok�Dex.
2) I don't know. That's a really good question.

1.The checkpoint in Route 11


2.He will pick the one who is stronger than yours

1) you get it from Oak's aid in the upstairs of the road building to the right of Vermilion City clso to where you find the first snorlax.

2) First off I do agree with you but in my opinion it makes the adventure more of a challenge and causes you to want to raise you pkmn more than his.

The reasons gary picks the one that plays your pokemon's weakness is because you will find that some Pokemon though the same level may be "stronger" from a "type" advantage in case you don't know, a type advantage is something like lightning is better to kill water, then say grass, it's basically that whatever attacks used are better for killing and better at lowering the other pokemon's hp down, sometimes it is so strong it can kill the other Pokemon straight away. I hope this helps and the item finder is found in the shack in Route 11 you need 30 Pokemon caught and professor oak's aide gives you an item finder.

Answer for #2 he does but luckily ,those pokemons only have normal moves (tackle ,ect) so don't worry .You'll have time to raise other Pokemon which have advantage against him.exapmle(choose Squirtle and he'll choose bulbasuar,after the first battle train a pidgey and he will be super effective on Bulbasaur!)

Anyway, I think he chooses a Pokemon to his advantage because he is not dumb to choose a Pokemon to your advantage.Hope I helped and best wishes for you to complete the game (because I did and I have 6 Pokemon on level 100 ,hahaha)

And keep collecting Pokemon (my Pokedex is about 300 speices!).

From King Of Hearts II

The itemfinder will be given by one of the aids of prof Oak.. After obtaining 50 pokemons (i guess)

Yah... Its a really nice question. Maybe to make the game more challlenging...