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There is no way to guarantee his entry to Canada unfortunately, but you likely will not run into issues since he is American.

As long as you are applying outland, it does not matter if you start the process before or after you enter Canada, nor will it have an technically have any impact on his likelihood of successful entry, since filing the PR app does not grant him any kind of status. He will be entering as a visitor either way.

My personal recommendation would be to file the app as soon as you are ready, and if you'd like to come to Canada while it's processing, don't do anything crazy (like sell your house in the US etc) until your husband has successfully entered Canada as a visitor.

Thanks so much for your advice! My husband has successfully entered Canada multiple times as a visitor before (most recent was July - for my sister’s wedding). The thing is, if we make this big life change, we WILL have to sell our house, and pack up all our belongings in order to move to Nova Scotia. This will all have to be planned well in advance so we can make this move. We are kind of “done” with our current house though and ready to move on regardless, but we will need to sell it and move all our furnishings, cat, vehicles, etc., to start our new life in Nova Scotia.
 
Thanks so much for your advice! My husband has successfully entered Canada multiple times as a visitor before (most recent was July - for my sister’s wedding). The thing is, if we make this big life change, we WILL have to sell our house, and pack up all our belongings in order to move to Nova Scotia. This will all have to be planned well in advance so we can make this move. We are kind of “done” with our current house though and ready to move on regardless, but we will need to sell it and move all our furnishings, cat, vehicles, etc., to start our new life in Nova Scotia.

It's possible you will have difficulty at the border if it appears your husband is attempting to move to Canada, rather than visit. The key to successfully entering as a visitor is just that - appearing as a visitor, not having too many belongings with you, and having proof that you still have ties to the US. If your husband shows up with you at the border with all your earthly belongings, vehicles, pets, in tow, you are pretty much guaranteeing he will not be allowed in.

Generally, people wait to make this kind of move until they are landing as a PR.
 
Thanks so much for your advice! My husband has successfully entered Canada multiple times as a visitor before (most recent was July - for my sister’s wedding). The thing is, if we make this big life change, we WILL have to sell our house, and pack up all our belongings in order to move to Nova Scotia. This will all have to be planned well in advance so we can make this move. We are kind of “done” with our current house though and ready to move on regardless, but we will need to sell it and move all our furnishings, cat, vehicles, etc., to start our new life in Nova Scotia.

Others can confirm, but as I understand you will be moving back to Canada as a "returned resident" and claim all goods tax/duty free, but your husband should be holding a visitor status. I am not sure how technically should it be done as far as entering Canada. May be you should enter separately with your child to avoid questions about his visitor status?
 
Hey guys. I read through this thread. It seems to apply to me pretty closely. I was born in Sudbury, ONtario and moved to the states with my mother at a young age. I became a naturalized American citizen when mother applied/became American and have lived here for ~25 years. My American passport shows that my birthplace is Canada, and I obviously have a Canadian birth cert. I married a fine lady in Colorado (american citizen) and we want to move to Canada for a fresh start, and I want to be close to my family for once in my life. We both have B. Sc. degrees and work in our respective fields. I've worked in the oil/gas industry as a geologist for about 8 years, and she is a physical fitness/yoga instructor. She also has experience in the restaurant industry.

I haven't had any luck landing a job myself only through applying for jobs on Indeed and Monster. I feel like it will be more realistic to get work once we are there, have an address, and can have face to face interviews. I am more than willing to work general labor until something more career oriente becomes available. We have money saved up for a house, but we just need to get there and get working in a reasonable amount of time. We plan to move in May/June. Since I am a Canadian citizen(right?), I can sponsor her? And how would we further convince Canadian gov that we are moving, besides making mention of our new adventure, and the fact that my entire biological family is in the immediate area of where we are intending to move? Can I use my father's address since we plan to live at his house while we find work and a house of our own...? Let me know. Feel free to PM me.


Thanks in advance.