Canadian visiting boyfriend for six months in US

My boyfriend, a Canadian citizen, is currently in the US, on and off, for a 9 month period acting as a consultant on a job for his company (not technically "working" in the US). I would like to go and stay with him for a little less than six months. I will be quitting my job prior to the visit. We have a house together in Canada, and I have some savings in the bank. The company will pay for us to travel back to Canada for weekend visits on a monthly basis. I will enter the US on my own (my boyfriend will enter the US separately), by car or bus, to fly from an American airport to our destination, but I will return to Canada for each visit crossing the border with my boyfriend. I'd appreciate any advice on border crossing and any potential problems I might have at Customs. Thanks.

As long as your Cdn residential ties remain strong, you should have no problem entering a as simple tourist (B2). The more you enter however, the more scrutiny you would face, and the more proof of Cdn ties you would need (utilty bills, etc).

Alternatively, if your Bf is in a work status, you are allowed to get a "cohabiting partner" B2 status, which would take the guess work out of each entry.

I would hope that your bf, while thinking he is "not technically working" in the US, has gotten the correct authorization when he enters.

Thanks for the input, AGN. My boyfriend had the appropriate documentation from his company explaining the nature of his activity in the US.
Does the fact that I will not be employed at the time I enter the US complicate matters? I am thinking that there might be less cause for the authorities to wonder if I might try to get a job in the US (I won't!) as my boyfriend is only there temporarily.
Also, If for some reason, at one of my return visits, I was denied entry, does that mean I could not enter the US at some time in the future?

Yes, not having a job is problematic, but only if you are entring us as a regular tourist, which can be overcome if your bf is in a work status (Like TN) rather than B1 business vistor. Explanations can help

The fact that you will be returning to Canada regularly is good in that it establishes a pattern of coming and going, rather than staying long 5-month stretches and returning to canada only for a weekend.

if you are ever denied entry, it will be for a reason (lack of Cdn ties, too much time in US, too little time in canada). Fix the issue and you will be readmitted.