Landing process & funds

I am planning to finish my landing process sometime in May 2006. Which is my closest port of entry as I am living in New York City? Also I am planning to move to Ottawa.

I am planning to complete my landing process now and come back to settle after six months. I am planning to take CAD 20,000 as a travelers check for the proof of funds.

I would like to deposit the amount only when I want to move permanently. Here are my questions

Can I bring back the travelers check to US?
Do I need to pay any taxes when I enter into US?
Do I need to pay any taxes when I re-enter into Canada?
To avoid taxes do I need to declare this in my goods to follow list or similar?
Is there any upper limit for us to bring money into Canada to avoid taxes?

I would appreciate your time.

Thanks,
John.