I don’t have an answer to the first one but for the second question, a few answers come to mind.
1) Yes, hishtadlus is important but we all know stories of big tzaddikim who rely (relied) entirely on emunah and somehow all their needs were taken care of. Hashem doesn’t need the hishtadlus of you buying the ticket in order for you to have the prize. Hashem is very creative and if Hashem wanted you to have, say, the free trip to Israel, you will get it whether or not you bought a ticket. But what if Hashem doesn’t think you deserve the free trip? That leads me to number 2.
2) Regarding raffles benefitting a charity, I believe that many who buy thinking they will win are relying on the zchus of their tzedaka to help them win something they weren’t necessarily meant to have.
Hashem doesn’t need your help to give you what you were meant to have. If you won the raffle, you were going to get that thing anyway, even if you hadn’t bought the ticket.