US Citizen visiting Canada: Specific help needed

[Redp0ny]

I'm interested in visiting my boyfriend in Canada for a long period of time (6 months ) in January 2016. I have many strange questions due to the nature of our circumstances.

1. I've been told I can still work during my stay since I telecommute and have a contract project with a company in the US - my work does not effect Canadian commerce/economy in any way. Is this a correct assumption?

2. I would be driving with him across a border in my own vehicle. I plan on bringing a bank statement with plenty of money for the 6 months, a letter from my workplace (if needed?) stating that I could take the 6 months off project for vacation, and a copy of a bill from my current address. Would I need anything else?

3. We would want to take a trip or two during my 6 month stay. It would be back to America to see my family. Will this be a problem for me or would Canada just let me back in once our trip is over?

4. Finally, my overall goal is to stay in Canada for 6 months, and extend my stay another 6 months while in Canada, so that we could apply for common law. If I applied for this extension, would I want to be honest and explain in the application that we desire common law status to continue our relationship together, or is that frowned upon.

Thanks for any advice

 

[scylla]

1. As long as your company does not have any Canadian clients / projects in Canada - yes.
2. You want to be able to demonstrate that you really are just a visitor to Canada and are not planning on trying to live here. Ideally you should bring additional evidence to demonstrate that you have strong ties to the US (e.g. proof of employment, proof of property ownership/rental, utility bills). You may not need this additional evidence - but it's better to have it with you just in case. Also, don't pack like you're moving. Try to only bring a couple of suitcases. Avoid bringing household and other items that make it look like you're moving (e.g. pots and pans, microwave, bed sheets, etc.).
3. There is never a guarantee you will be allowed back into Canada. Each time you re-enter the country, you will be examined as a new visitor and there is always some chance you may be refused.
4. When you apply for the extension you should certainly say that you are working towards common law. This typically guarantees the extension will be approved.

 

[Redp0ny]

Thank you so much for the help.

My biggest concern is having to go on those trips in the middle of this extended stay. Do they look at how many times I've entered and left to make the choice? I'm wondering if I go on the trip at month 3 of our 6 month term, can I come back to Canada and request 6 months all over again - it restarts? Haha sorry if this is a weird question, I just want to have my ducks in a row to make this work, and this family trip is something I probably can't miss.

 

[scylla]

Yes - sometimes they will look at how often you're entering and exiting Canada to determine if you will be allowed in and for how long. Again, keep in mind that you are only allowed to visit Canada at this time. If you start behaving like someone who lives here - this can sometimes land you in trouble at the border. (Having said that, what happens is ultimately up to the officer you encounter at the border.)

You can certainly request another six month visit when you re-enter - but again, whether or not you're given a six month visit is entirely up to the officer.

 

[Redp0ny]

Thank you very much.

This is the trickiest part. The trips will be literally a month or so after I initially drive up to Canada, so I'm wondering if the "safer" route is to say I'm only staying for a month when I first drive through the border, then say 3 months after I go through customs at the Canadian airport. I will still carry all the paperwork, but by a few months in the bills I'll have showing my address will be a few months old (unless I can get my friends to forward me new ones.)

My goal is to remain in Canada as long as possible to apply for Common Law.