no you need a passport
Yes, Canadians can visit Cuba. Canadian citizens are required to have a valid passport and tourist card to enter Cuba. Additionally, they must have proof of travel health insurance coverage for the duration of their stay in Cuba.
It makes no difference where you were born. I believe you must be a citizen of the US in order to get a US passport.
Getting a Canadian passport has rules. It is not contingent on where you are going. Canada and Cuba have good relations. I cannot see that there is any particular waiting period for this
Indeed, even if it was a direct flight.
Yes, and you'll be pleasantly surprised at the level of service when you get there. All you need is a current passport.
No. Cuba does not recognize the State of Israel.
Americans certainly can enter into Cuba. There is no law stating that Americans could not enter into Cuba's small territory.
Yes, you still need a visa to show that you are a US resident. This is to ensure your safety.
Yes
Yes. You need a passport to fly anywhere.
No, you don't need a visa for traveling to Canada if you have a Dutch passport.