Do you find any difference in quality between your rural vs city accountant? I'm wondering if paying more actually gets you better service or tax savings?

Honestly, my rural accountant is more attentive and responsive - probably because she has fewer clients overall. The Chicago firm has more specialized expertise in certain areas (particularly for e-commerce tax issues), but for day-to-day service and general tax matters, the rural accountant provides better value. The big difference is that the Chicago firm has more specialists under one roof, so if I have a very specific tax situation, they can usually handle it in-house. With my rural accountant, she occasionally needs to bring in outside expertise for complex situations. But for standard business tax planning and preparation, I haven't found that paying more necessarily results in better service or outcomes.

How do you find a good EA? Is there a directory or certification board? I've only ever used CPAs and H&R Block type places.

You can find qualified EAs through the National Association of Enrolled Agents website (NAEA.org) - they have a directory searchable by location and specialization. I found mine through a business owner networking group, which was great because I got to hear about direct experiences from other small business owners. When interviewing potential EAs, ask about their experience with your specific industry and business structure. A good EA should be able to discuss relevant deductions and planning strategies in your initial consultation. Also check if they offer audit representation (most do, it's a core part of their expertise). The right EA can provide the same level of tax expertise as a CPA, often with more specialized tax knowledge and lower fees since they focus specifically on taxation rather than broader accounting services.

That's really helpful. So for my invoices, should I format it as "My Full Name dba Business Name" and then just use my SSN on the W9 form? Or should I include both the SSN and FEIN on different parts of the form?

You should format it exactly as "Your Full Legal Name dba Business Name" on your invoices, and then on your W9, check the "Individual/sole proprietor" box, use your personal name on the "Name" line, your business name on the "Business name/disregarded entity" line, and your SSN in part I. You can include your EIN in Part II if you want, but it's cleaner to just use your SSN for everything unless you specifically need the EIN for something like business banking. This way, everything matches what the IRS has on file for you personally, which prevents these verification hiccups.

From my experience (worked in tax prep for 7 years), these kinds of mismatches don't typically trigger audits on their own. They're considered administrative issues rather than compliance problems. The IRS is looking for income reporting discrepancies, not ID formatting issues.

That's a really good point I hadn't considered. My first payment is supposed to be due on May 15th according to what I set up in TurboTax. Should I just go ahead and make that payment to the IRS directly if I still don't have confirmation by then?

Yes, absolutely make that May 15th payment even without official confirmation. You can pay directly through the IRS Direct Pay system on their website - just make sure to select the correct tax year and payment type (installment agreement). This way you're covered no matter what. If your payment plan is already in their system, the payment will be correctly applied to it. If there was some glitch and the plan wasn't properly set up, you've still made a payment toward your tax debt before any serious penalties kick in.

It happened to me once! Turned out TurboTax had a transmission error with that part of my return. I had to call the IRS and set up the payment plan directly with them. They were actually pretty understanding about it and didn't charge me any late fees since I could prove I tried to set it up on time.

Thank you for bringing up these important points! I have about $35K combined in my Canadian accounts, so I'll definitely need to file the FBAR. You're right about the TFSA - that's exactly why I'm planning to close it before October. Regarding RRSPs, I do have about $80K in an RRSP. I wasn't aware of Form 8891 - does that need to be filed annually or just once?

The good news is that Form 8891 was actually eliminated in 2014! The IRS now automatically recognizes the tax deferral for RRSPs under the US-Canada tax treaty without requiring a specific form. You'll still need to report the existence of the RRSP on your FBAR and potentially on Form 8938 (Statement of Foreign Financial Assets) if you meet the filing threshold, but the income can continue to grow tax-deferred. One other consideration for your plan: make sure you've researched any state-specific requirements. California, for example, doesn't always follow federal treatment of foreign income and may have different rules regarding your Canadian accounts and investments compared to federal regulations.

This is incorrect information. Canada doesn't have an "exit tax" in the same way as the US. What Canada has is a deemed disposition rule where certain properties are treated as if they were sold at fair market value when you cease Canadian residency. However, this typically doesn't apply to cash, personal-use property, most registered plans like RRSPs, and certain real property located in Canada.

Thanks for bringing this up. I've been concerned about this potential issue. My total assets are around CAD $1.3 million, so I should be under that threshold. Most of my assets are either in my RRSP, cash, or the condo which I'm planning to sell before becoming a non-resident. Would there be any other assets I should be concerned about for the deemed disposition rules?

8 Wait really? So even if they get married on December 31, they're considered married for the WHOLE tax year? That seems weird... does that mean you could strategic time your wedding for tax purposes?

15 Yes, that's exactly right. The IRS only cares about your marital status on the last day of the year. If you're married on December 31st, you're considered married for the entire tax year. And yes, some people do strategically time their weddings for tax purposes, though I wouldn't recommend making such an important life decision solely based on taxes! But it's something to be aware of as you plan. In some cases, delaying a December wedding to January could be beneficial, while in other situations (like the original poster's with disparate incomes), getting married before year-end might save money.

2 I disagree - their withholding seems reasonable. The effective tax rate for someone earning around $570k would be close to 20% after deductions, and they're at 18.5% with a quarter of the year left. They're probably on track.