Don't forget about the GST/HST (Goods and Services Tax/Harmonized Sales Tax) in Canada vs. sales tax in the US! This actually makes a significant difference in day-to-day costs. In Canada, GST is 5% federally, plus provincial sales taxes that are either separate or harmonized with the GST. Total sales taxes range from 5% in Alberta to 15% in the Atlantic provinces. In the US, sales tax varies wildly by state and even by county/city. Some states like Oregon and New Hampshire have NO sales tax, while others like California can have combined state/local rates approaching 10%. This might not seem like a big deal compared to income tax, but on day-to-day purchases over years, it adds up to thousands of dollars difference.

One major factor that hasn't been discussed yet is the Alternative Minimum Tax (AMT) differences between the two countries. In the US, AMT can catch high earners by surprise, especially those with significant deductions or stock options. At your $220k income level, you could potentially trigger AMT depending on your deduction profile. Canada eliminated their federal AMT in 2023 (though it's being reintroduced in modified form), but the calculation works very differently than the US version. Canadian AMT historically applied to fewer taxpayers but had different triggers. Also consider property taxes - they're generally much higher in Canada. For example, Toronto property taxes can be 0.6-1.2% of assessed value annually, while many Texas cities are 2-3% but on lower assessed values due to homestead exemptions. This can significantly impact your total tax burden if you're planning to buy property. The timing of when you pay taxes also differs. Canada requires more frequent installment payments for high earners, while the US allows more flexibility with quarterly estimates. Just another practical consideration for cash flow planning.

You made the right call getting an EIN for privacy protection! I've been using one as a sole proprietor for about 3 years now and it's worked great. Your tax guy was probably being overly cautious - there's really no downside from a tax perspective. The key thing you mentioned about the business name is important though. Since the IRS has a business name on file for your EIN, you should definitely use that same name consistently on all your W9 forms and other business documents. Leaving it blank could create matching issues when clients file their 1099s. I learned this the hard way when a client's accounting department rejected my W9 because the business name field was blank but my EIN was clearly for a business entity in their system. Now I always use the exact name from my EIN confirmation letter and haven't had any issues since. One more tip - keep a copy of that EIN confirmation letter handy. Some clients or their accounting firms will ask to see it to verify the information matches your W9.

You're absolutely on the right track with getting an EIN for privacy protection! I did the same thing when I started freelancing and it's been a game-changer for peace of mind when sharing tax info with clients. Your tax guy's concern is understandable but outdated - many accountants still think EINs are only for businesses with employees, but the IRS explicitly allows sole proprietors to get them for privacy reasons. There are zero tax complications since everything still flows through to your personal return on Schedule C. The business name issue you mentioned is crucial though. Since you left it blank on your W9s but the IRS has a name on file, you could run into problems when clients file their 1099s. I'd recommend going back to recent clients and submitting updated W9s with the exact business name from your EIN letter. It's a small hassle now but will save you major headaches during tax season. Also, make sure you're not mixing your EIN and SSN across different clients - pick one and stick with it consistently. The IRS matching system can get confused if the same person is receiving 1099s under both numbers.

I'm dealing with a similar situation as a W2 commissioned employee in real estate. One thing that helped me was documenting EVERYTHING - not just mileage, but all the indirect costs like increased insurance premiums, accelerated depreciation, and maintenance tied to business use. Even though I can't deduct these federally right now, having detailed records helped me make a stronger case to my broker for establishing a reimbursement plan. When I presented the total annual cost (not just gas money), it was eye-opening for management. My calculation showed I was effectively subsidizing about $8,000 per year in business operations out of my own pocket. That made the payroll tax savings from an accountable plan look even more attractive to them. Also, don't overlook the depreciation aspect - business miles put significantly more wear on your vehicle than personal driving. I started tracking this separately and it added substantial weight to my reimbursement request. The IRS standard mileage rate exists for a reason - it reflects the true cost of operating a vehicle for business purposes.

Just wanted to share my experience as someone who successfully negotiated an accountable plan after being in this exact situation. I'm also a W2 commissioned sales employee who was driving about 20k miles annually for customer visits with zero reimbursement. The key was presenting it as a win-win business solution rather than just asking for help with my expenses. I calculated that my employer could save about $1,280 annually in payroll taxes by reimbursing my mileage versus giving me an equivalent salary increase. For context, at 20k miles × $0.67/mile = $13,400 in annual reimbursements, they'd avoid 7.65% employer payroll taxes they'd otherwise pay on $13,400 in additional wages. I also emphasized how the accountable plan would help with employee retention and recruitment. Quality sales people are expensive to replace, and vehicle costs are a real factor in job satisfaction for field-based roles. The documentation requirements aren't as burdensome as they initially seem - I use a simple smartphone app that tracks GPS automatically and just requires me to add the business purpose. Monthly submissions take maybe 20 minutes total. One tip: Start with a 6-month pilot program proposal. It's less intimidating for employers and gives everyone a chance to see how it works in practice. My company made it permanent after seeing how smoothly it ran and realizing the actual tax savings.

Has anyone looked into whether the premium reimbursement needs to be included on your W-2? I'm in a similar situation but my accountant is including the reimbursed amounts in Box 1 of my W-2 even though I'm not an owner.

I'm dealing with a very similar situation right now! My family's S-Corp just went through this exact issue with our accountant. What we discovered is that many accountants get confused about the ownership attribution rules and mistakenly apply the 2%+ shareholder restrictions to ALL family members, even when they have zero ownership. The key distinction is actual ownership vs. family relationship. Just because you're related to the owner doesn't automatically make you subject to the shareholder rules. Since you explicitly stated you have no ownership stake and receive a regular W-2, your health insurance premiums should be treated exactly like any other non-owner employee's. I'd suggest asking your accountant to show you the specific IRS code section they're relying on for their position. The attribution rules in IRC Section 318 only apply when determining if someone is a more-than-2% shareholder - they don't automatically disqualify family member employees from standard employee benefits if those family members don't actually own stock. Your situation sounds straightforward - you should be able to maintain the same health insurance deduction treatment you had as a C-Corp employee.

Important thing to know - if you're expecting refunds, you only have 3 years from the original filing deadline to claim them. So for example, 2020 refunds can still be claimed until April 2024, but anything before that is gone forever if you were owed money. BUT if you owe the IRS money, there's no time limit on when they can come after you. So definitely better to address this proactively like you're doing now!

I went through something very similar about 3 years ago - hadn't filed for 6 years due to a combination of job changes, a messy divorce, and just pure avoidance anxiety. The longer I waited, the more terrifying it seemed. Here's what worked for me: Start by getting your Account Transcript from the IRS online (irs.gov). This will show you if they've already filed substitute returns for you (which they sometimes do if you have W-2 income). If they have, you'll see exactly what they think you owe. Don't try to tackle all years at once - it's overwhelming. I started with the most recent year and worked backwards. Focus on getting accurate numbers rather than rushing through everything. One thing that really helped my anxiety was realizing that the IRS actually wants to work with you once you make contact. They have payment plans, penalty abatement options, and they're generally reasonable if you're making a good faith effort to comply. The relief of finally addressing it is incredible. Yes, there will be some penalties and interest, but it's probably not as catastrophic as your anxiety is telling you it will be. You've got this!