🗽 COUNTRY A New York VS 🍁 COUNTRY B Canada

Yes. All US citizens and green card holders must file a US federal tax return regardless of where they live. New York state tax ends once you successfully establish non-residency from New York (which is notoriously difficult — New York aggressively audits high-income departing residents). Your US federal obligation continues indefinitely. The US-Canada tax treaty allows you to claim foreign tax credits on Canadian taxes paid, preventing most double taxation.

Yes. New York State is one of the most aggressive states for pursuing former residents. You must establish domicile in Canada, spend fewer than 183 days in New York, and not maintain a permanent place of abode in the state. High-income New Yorkers are frequently audited for 'statutory residency' — if you maintain an apartment in New York and spend more than 183 days there, New York will tax you regardless of where your domicile is claimed to be.

A New York City resident pays state tax (up to 10.9%) + NYC city tax (up to 3.876%) + federal (up to 37%). At $100,000: ~$5,398 NY state + ~$3,100 NYC + ~$17,344 federal = ~$25,842 total. Canada (Ontario) at $100,000: ~$24,385. Surprisingly, total NYC burden is slightly higher than Toronto at $100K. At $150K+, the comparison remains close.

Wall Street (New York) typically offers higher USD base salaries than Bay Street (Toronto), particularly for investment banking, private equity, and hedge funds. However, Toronto's financial sector has grown significantly. After-tax income comparisons depend heavily on whether you work in midtown Manhattan (NYC city + state + federal) versus downtown Toronto (federal + Ontario). The gap in absolute after-tax income is smaller than the headline tax rates suggest.

Yes. Ontario's OHIP (Ontario Health Insurance Plan) provides universal healthcare funded through taxation. New York residents typically pay $400-$800/month in health insurance premiums (or have employer coverage). This healthcare value offsets some of Canada's higher income tax burden when comparing total cost of living.

Americans with Canadian bank accounts must file FBAR (FinCEN Form 114) if aggregate foreign account values exceed $10,000 at any point during the year. FATCA Form 8938 is required for higher thresholds ($50,000-$200,000+ depending on filing status and residency). Canadian RRSPs and TFSAs have specific US reporting requirements. Greenback Expat Tax Services specialises in these filings for US expats in Canada.