Deether said:
1. We plan to do an outland application for permanent residency as we've heard these are processed faster. Is this recommended?
Outland is definitely recommended for US citizens. The only real downside is that she'd have to go to the US for an interview if one is required.
2. Obviously she won't be granted PR by the time we move. How will the process go when we arrive at the border? Will they let her in on a visitor visa, until the PR app goes through? Will it be a problem that we'll be moving with all our personal effects? I mean, will it be questionable why she's getting a visitor visa, but moving with all her stuff? Is this the recommended way to do this?
No, this is definitely not recommended. She could be banned entry to Canada for as long as 1 or 2 years.
If you (personally) are moving back to Canada with your own personal (used) effects I believe that you can do it without paying duty or GST. Offhand, I don't remember where you find information on this, but I know others have discussed it.
As for your wife, she can't just suddenly move to Canada with all her personal effects, so it would not be wise to move her stuff and your stuff together. Well, maybe it won't exactly be "unwise" but it certainly will complicate things a bit if it's all mixed together.
Technically, she won't be on a "visitor visa" since US citizens are visa exempt, but she will be on a visit. You'll have to satisfy them that she's only visiting for now, even though she is also applying to move permanently later, assuming the PR application is successful.
At the border, they'll want you to prove that you have applied for PR (show a receipt that you paid for it, and a copy of the forms filled out might also be good to have on hand). You'll want to have proof of your wedding. For a visit, you'll need to show that she has significant ties to the US, and thus a reason to go back. A job in the US, property that she owns there, family that she has to look after, or other significant ties would all be good. I suspect you might be a little weak in that department.
You should be with her when she enters Canada for her visit. They are not required to, but they will likely allow her to visit Canada while the application is being processed, so long as they don't think she'll overstay her permitted visit period. If they are happy that she is just visiting and not moving permanently (yet) they will probably issue a "Visitor Record" (VR). This is a piece of paper attached to her passport that has to be surrendered at the border when she leaves before the expiry date.
Most outland applications processed through Buffalo NY are currently taking about 5-11 months, so they will normally issue a visitor record for 6 months. You can apply to extend that 30 days before it expires (at a fee of $75) and you will usually get an additional 6 or 12 months if the PR is not approved during the time of the first VR.
What she should bring is the sort of things that anyone would bring for a visit of a few months (no more than 6). When I brought my partner across the border, we were lucky they didn't go through all the stuff we had stuffed into every crack and crevice in the car, because it was on the borderline of being a bit too much. The one thing they did ask us was whether we had any furniture, and they didn't examine any further.
We stored some stuff (including furniture) in a storage unit on the other side of the border, so we didn't have stuff that red-flagged that we were doing a permanent move. If you can leave some of her stuff with a relative or in some kind of storage, it will be much more believable that she is visiting and not moving.
3. Should I use my Canadian or US passport when I cross the border?
Definitely use the Canadian passport when coming into Canada. You can't be denied returning to your own country. Of course, if you are sponsoring your wife, you do want to show that you are Canadian.
4. Will she only be eligible for Canadian health care once her PR status is granted? If so, I was looking into getting COBRA insurance from my work, but it's about $600 a month. Are there cheaper insurance options she could use in Canada?
Health care is a provincial responsibility, so it's not the same in every province. Some provinces have a 3-month waiting period, while others allow you health insurance on the day of landing.
I think I must have forgotten something, but that's the gist of it. Oh, if you haven't sent the application yet, get anm FBI police check ordered right away. They say 8-10 weeks, but sometimes they take much longer. You want to have that before you send in the application, so that can hold everything up. That's my personal problem at the moment. My partner only got a 3-month VR and just applied to the FBI a week before. Doing the math, you'll see that it's iffy whether he will have the FBI check (and be able to send in the PR app) before he has to apply to extend his visit.
