Snowbird Part 2

With the loonie trading below the 90 cent range it will be a more expensive year for those who haven’t hedged their bets by also owning U.S. dollars.  At some point you may find convenience in establishing a bank account in U.S. $ either here or below.  A U.S. dollar credit card may be of benefit too.
Stopping in gambling meccas is popular but be prepared to pay a withholding tax of 30% on any substantial winnings for most, but not all, games of chance. The good news is that you can off-set if you can prove the year’s losses.
Most Canadians are not planning on becoming a U.S. resident so limit their stay to less than the 183 days in a year they are allowed by using the clause known as the Closer Connection Exception.  If your visit comes under scrutiny you may need to file IRS form 8840.
Property purchase, ownership and income from U.S. based property bring on further challenges in terms of tax filing and potentially, estate planning issues.
All diversified investors will own shares in companies domiciled in the U.S..  If you own individual shares they may create dividend income.   The current tax treaty ensures that 15% of this income (excluding RRSPs and RRIFs) is remitted back to the U.S..  To avoid double taxation the CRA offsets with a tax credit.
Mortgage lending to Canadians is becoming easier for property purchase but has its’ differences.  For one, your payments will be in US $.  Unless you have rental income the tax deductibility of mortgage interest is of little benefit.  Your exit strategy also needs more preparation as the net gain after improvements and depreciation will be taxable and a U.S. tax return will need filing requiring a U.S. Individual Taxpayer Identification Number.
Estate strategies and planning are compounded if you own U.S. property at death. I will defer to those in the legal and accounting fields specializing in this niche but point out that Canada’s system is largely based upon income while in the U.S. it is based upon assets owned.
Watching a couple of episodes of Border Security shows how seriously frontline workers take their jobs.  They are experts at detecting little lies and begin to circle like sharks when you provide anything less than full disclosure.  Limited discretion may allow you the right of access while untruthfulness may result in penalties, denial or a return engagement with the judiciary.
Best to be well-prepared by knowing in advance.