Seeking general advice

Hi: I am a 57-yr old Canadian man engaged to a 55-yr old American lady. We are professionals comtemplating retirement and tentatively plan a summer 2010 wedding. The plan is to base ourselves in NY State so she can care for her elderly mother but we also need to maintain a home in Canada as I have two College aged children. We both will be able to find contract work in either country if allowed.
1. Can we travel and work in both countries?
2. What Canadian benefits could I lose if I obtained a US Green card?
3. We also want to know if we would cause ourselves problems if we got married before applying for the appropriate visas.

Most important...How should we proceed with respect to US and Canadian laws.
Oh, by the way, after 35 yrs and some previous marriages, two best friends from College are getting married. Life's great!

1. Can we travel and work in both countries?

travel yes, work, not without proper authorization

2. What Canadian benefits could I lose if I obtained a US Green card?

if you're refering to provincial healthcare benefits, you will lose those. If you're referring to retirement benefits, you can still claim those at the appropriate age, and receive payments while living in the US

3. We also want to know if we would cause ourselves problems if we got married before applying for the appropriate visas.

depends. see http://www.visajourney.com for marriage based immigration info to the US

Most important...How should we proceed with respect to US and Canadian laws.

see link above for US immigration info. If your plan is to live in the US, what Canadian laws are you referring to?

Oh, by the way, after 35 yrs and some previous marriages, two best friends from College are getting married. Life's great!

Congratulations

The plan is to base ourselves in NY State so she can care for her elderly mother but we also need to maintain a home in Canada as I have two College aged children. We both will be able to find contract work in either country if allowed.
1. Can we travel and work in both countries?
2. What Canadian benefits could I lose if I obtained a US Green card?
3. We also want to know if we would cause ourselves problems if we got married before applying for the appropriate visas.

Most important...How should we proceed with respect to US and Canadian laws.

We've had this thread several times on here, it usually boils down to the fact that it's not worth the hassle of getting married because you want to move between countries and estate/tax planning and so on gets very complex.

Certainly you can travel and work between countries, but if you become a US LPR your tax home automatically becomes the US and you must file jointly in the US. So you lose Canadian healthcare for example, because you must sever residential ties to Canada and things like an RESP become complex (although you can keep your RRSP).

You have to get married to be sponsored by your spouse to move to the US, unless you want to do the K-1 fiance route which isn't advisable because it's more long-winded and expensive.

As a US LPR it becomes very tricky to work outside of the US, once you're a citizen it's not so hard but there are residency requirements to keep LPR status, plus you cannot move your tax home from the US as an LPR which also makes life complicated.

As far as the house in Canada goes, you can have two houses, but based on what I've seen on here in the past this is usually where the marriage plan starts to get messy because if you're married you can only have one principal residence - which means the other house becomes subject to capital gains tax. If you're single then you can each have a house.

The way the law works it's designed around a married couple where you both live together and generally speaking work in the same country. It's not impossible to have more than one house and work in different countries but it's more complicated (and expensive) than if you're single.

Sometimes it works, the most common major tax fiddle there is I'm sure is to marry someone and have them live in a tax haven like Monaco and then you can claim residential ties to Monaco wherever you are and only pay payroll taxes for wherever you're working.

Different scenario though with the US and Canada because of the way the immigration and tax laws work, the US for example requires all LPRs and citizens to file a US tax return wherever they live and also there is a "foreign exclusion limit" which means you face US taxes even on foreign-earned income from employment abroad over the limit (currently $87,600). This was specifically thought up expressly to stop US citizens avoiding US taxes by moving their tax home abroad to places like Monaco and the Cayman Islands.