The USA has no obligation to allow entry to someone who is NOT a Canadian citizen. Your immigration status in Canada means nothing to the US government. They decide who can enter their country, or not.
yes
Yes. In September of 1939. The US didn't enter until December 7, 1941.
yes, all entry into Canada is required to have a passport, you'll need it to re-enter the US anyways.
It depends what country your passport is from. Some countries don't need visas to enter the US temporarily, but most do. Search "visitor visa to US" for a list of countries. Multi-EntryCanadian visas allow visitors/workers/students with visa requirements to travel to foreign countries and back. Single-entry visas allow visitors to travel within the continental North America and back without requiring a new visa as long as all other requirements are met and they have legal status inside Canada.
file a petition for him
The USA has no obligation to allow entry to someone who is NOT a Canadian citizen. Your immigration status in Canada means nothing to the US government. They decide who can enter their country, or not.
If you overstayed less than 6 month you will be banned to entering the US for 3 Years, and if you overstayed more than 6 Month you will be banned for 10 Years (AG)
No, plenty of people come to US "legally", and they are "legal" as long as their status is legal. Currently, illegal immigrants who came to the US without inspection - border jumpers, has no way to adjust their status to a legal one. Others who overstayed, etc, could possibly adjust their status under different classes.
I am not certain what you mean by "options" but your status is a US citizen which means you would be required to obtain a US passport to enter Canada. If your father still holds Canadian citizenship you might be eligible for dual citizenship but that would be determine by Canadian laws not US laws.
yes.
Alaska
yes
Even Infants can enter the US with their US passport. So there is really no age limit to one who wants to enter as long as they have appropriate documents.
Not necessarily. However, if you are eligible or have the documents for your travel to Canada, then yes, you can enter Canada.
6 months
well, i guess they could ask?