Going cross-eyed with all these visas

OK so here is the situation. I am currently dating an American, and there is talk of me moving to him (he may move here, but chances are, he has the better job, i would move there).
What I'm getting confused about is all the visas that are out there.
I am a Canadian citizen, have been working at the same job for the last 6 years. But the problem is, I work in a travel agency, and I doubt that American is dying to hire a Canadian to work in travel.
I'm not sure how the visas work, because they seem to want professionals.
I also have a sister who has been in the us for over 20 years, I know there were visas that family members could sign for, but I don't know if this applies.
Is there anyone out there that might be able to help me in the right direction?

Yes,
Most employment based VISA are gear towards professional.

Family based visa takes long long time. Especially siblings based.
I think it is around 10 years deadlock.

If you think you are not quite qualify for employment based visa and the family one takes too long, the fastest one is a marriage visa.

eeek, marriage visa is a bit too soon for us.

I-130 for siblings currently takes 8.5 years, if you're lucky. (She must be a US citizen).

There is essentially no such thing as a work permit for people in non-professional positions to enter the US. Lot of "ifs, ands and buts" to that one, but that's the gist of it. (Seasonal agricultural workers is the biggest "but", but I'm assuming that one isn't for you. Personal servants who've been employed for at least a year outside the US is another one.) An employer can sponsor people without specialised skills in EB-3 unskilled status, but the wait time for that one is many years.

On the bright side, "co-habiting" partners can stay in the US in B-2 status indefinitely, but you can't work in B-2 status. (I'm not sure if that applies if the partner is a US citizen though).

Only other option really is K-1 (fiancée) or K-3 (spouse).

You'd be in a similar position the other way around, although it's easier to get work permits for people to work in Canada. Plus Canada recognises "common-law" marriage, so you don't actually have to get married.

Boo urns to America not wanting me!
My sister has been in the US for about 20 years, but she only has an alien status, so even if the sibling thing didn't take 8.5 years, I don't think it would qualify. and any other relative I have that is American lives in Canada.
I am going to see if I can contact someone at a consulate to see what I should do.

any other relative I have that is American lives in Canada

Doesn't matter, they can file an I-130 for you regardless of where they live. They will have to file with the nearest US consulate that deals with them, which I think is Toronto (maybe Ottawa). But they must be an immediate family member, parent, sibling, child. Not a quick process though, although it's pretty simple. If it's a sibling they must be a US citizen though, your sister could get US citizenship but obviously that would take awhile, I think the current average wait is 15 months. So you're looking at nearly ten years. :s

Ah, see the only other person is my neice, and I doubt she's going to sign anything to let me move away!
Well I'll keep in talks with my boyfriend, I know he's vying for me to move there, but it seems that it's easier to get to Canada at this point.
I will have to do some sweet talking