His Pokemon might be a bit confused at first. Pikachu, for example, is used to their adventures on the road. But they'll soon adapt. They could make new Pokemon friends at the school too. And they'll be there to support Ash during his school challenges, like in battles or tests.
Ash's Pokemon would likely have mixed reactions. Some like Bulbasaur, being the gentle and observant one, would be quick to accept Sabrina. It might even enjoy the new psychic powers that Sabrina could bring into their group. However, Squirtle might be a bit mischievous at first, trying to test Sabrina's patience. For Sabrina's Pokemon, Alakazam, being highly intelligent, would sense Ash's good intentions towards Sabrina and would support the relationship. Her other Pokemon would follow Alakazam's lead.
Ash might be initially shocked and scared. But he's a brave trainer. He would quickly gather his courage and probably try to figure out who sent the hitman. He'd use his detective skills, which he has developed over his many adventures.
Ash would be extremely heartbroken. He might cry a lot and be in a state of shock at first. Then he would probably feel angry at the situation that led to Gary's death, whether it was a villain or just a dangerous accident. Ash would also feel a strong sense of responsibility, as if he has to carry on Gary's unfulfilled dreams.
I think Ash would be angry as well as hurt. He's a passionate trainer and his friends mean a great deal to him. He might challenge May in a Pokémon battle, not to defeat her but to make her see how wrong her betrayal is. And during the battle, he would keep asking her to come back to their old friendship.
Ash would be extremely hurt. He's a very loyal person, and having someone he cares about like Lillie betray him would be a huge blow. He might initially go into denial, not believing that Lillie could do such a thing.
Pikachu might be very confused at first. When it sees 'Ash' (really May in Ash's body) acting differently, it could be hesitant to follow commands as usual. For May's Pokemon, they might be surprised to see 'May' (Ash in May's body) suddenly having a more battle - oriented attitude. For example, May's Beautifly might be confused when 'May' wants to train it for battles instead of focusing on its appearance for Contests.
His Pikachu would probably be very supportive. It would stay by his side as he studies, maybe even help him in small ways like fetching medical tools. It trusts Ash completely and would be happy to see him pursue something new.