I am not qualified in any way to comment on most of your questions but I will try to answer some of them:
- duties, etc. - usually not an issue if you have your watches shipped via the postal service. EMS transfers over to Canada Post one it hits our shores. STAY AWAY from FedEx or UPS.
- 44 mm is not too large.
- if you want years of good service, I think you should be looking at quartz watches. The mechanical ones (from what I can see) will eventually need service or just die.

Hope this helps. Should meet up sometime to compare notes.

Rod