To land in Quebec or transit?

Hi Everyone, here is the thing, I can enter Canada without visa, I have bought a ticket from Montreal to Latvia, to go see my parents. I will be going from Vermont USA to Quebec in a friends car and fly out, then come back after a month to Canada for good. I am not going to continue to keep my H1b status (note I have no H1b visa in my passport) in USA.
The questions are :
1) to land on Sunday (I have an address in Montreal already, a friend) and fly out the same day?
2) Or use my passport to enter without landing (if that is possible) and land when I come back from Latvia.
3) Do you think if I come back as landed immigrant without PR card they will let me in based on my visa free passport? Or should I do the travel document in Latvia?
4) If I decide to land and leave shortly, I will be carrying little stuff with me, just for the trip, will that be suspicious to IO?
Thank you very much! With all the US immigration issues I became Paranoid about visas and stuff.