Thanks everyone for all the helpful information! As someone who just went through incorporating my freelance business in Canada, this thread has been incredibly valuable. I want to add one more tip that saved me some headaches: make sure your Canadian business registration information (business number, registered address, etc.) exactly matches what you put on the W-8BEN-E form. Apple's tax validation system is pretty strict about consistency between documents. Also, if you're like me and procrastinated on getting your CRA business number, you can actually get it online instantly through the CRA website once your corporation is registered. You don't have to wait for mail anymore - they give you the number immediately after completing the online application. The combination of properly completing the W-8BEN-E for the 0% withholding rate AND making sure you're enrolled in the Small Business Program for the 15% commission rate can make a huge difference in your bottom line. Don't forget about either one!

This is an incredibly thorough discussion! As someone who works with international tax compliance, I want to add a few additional points that might help other Canadian developers: 1. **Documentation retention**: Keep copies of your submitted W-8BEN-E and any correspondence with Apple. The IRS can request these during audits, and having proper documentation of your treaty claim is crucial. 2. **Quarterly estimated taxes**: Don't forget that as a Canadian corporation earning US-source income, you may need to make quarterly estimated tax payments to the CRA. The reduced withholding from the treaty means less tax is being withheld upfront, so plan accordingly. 3. **Transfer pricing considerations**: If you have any related entities or if your business structure becomes more complex, be aware of transfer pricing rules. This isn't usually an issue for simple owner-operated corporations, but it's worth understanding if you plan to expand. 4. **State tax implications**: While the federal W-8BEN-E handles federal withholding, some US states have their own sourcing rules for digital products. Most don't tax foreign corporations on royalty income, but it's worth researching if you have significant revenue. The resources mentioned in this thread (taxr.ai for form guidance and Claimyr for IRS contact) seem to have helped several people navigate this successfully. Good luck with your incorporation!

Coming from a similar corporate accounting background, I made the transition to tax preparation two years ago and can relate to everything you're describing. The seasonal nature was actually one of the biggest draws for me - having that intense period followed by time to recharge and plan for the next year has been much better for my work-life balance than the constant grind of corporate deadlines. One thing I'd add to the great advice already shared: don't underestimate the importance of practice management systems early on. I started with basic spreadsheets to track clients and quickly realized I needed something more robust as my client base grew. Investing in good client management software from the beginning helps you look professional and keeps you organized during those hectic peak season weeks. The learning curve is definitely manageable, especially with your accounting background. Tax software has become incredibly sophisticated - it'll catch most errors and guide you through complex situations. What really matters is developing the soft skills for client communication and learning to translate tax concepts into language regular people can understand. One unexpected benefit I've found is how much this career has improved my own personal financial knowledge. Working with hundreds of different tax situations has given me insights into investment strategies, retirement planning, and tax optimization that I never would have learned in corporate accounting.

As someone who recently made this exact transition from corporate accounting to tax preparation, I can't emphasize enough how rewarding this career change has been! The client interaction aspect that drew you in is absolutely the best part - there's something incredibly satisfying about helping a young family discover they're getting a substantial refund, or walking a small business owner through deductions they didn't know existed. From a practical standpoint, your corporate accounting background will be a huge advantage. You already understand the fundamentals, so you'll mainly need to learn the individual tax code differences and develop your client communication skills. I'd recommend starting with your PTIN and then working toward EA certification - it really does open doors and allows you to command higher fees. The seasonal income variability was my biggest concern initially, but it's entirely manageable with proper planning. I budget based on my lowest-earning months and treat peak season income as a bonus for savings and business investment. Many preparers I know supplement with bookkeeping, payroll services, or even financial planning during slower periods. One piece of advice: shadow an experienced preparer for a few days if possible, or volunteer with VITA to get some hands-on client experience before making the full leap. The technical skills are learnable, but seeing how professionals handle difficult conversations and manage client expectations is invaluable. The profession definitely has its challenges, but for someone seeking more meaningful work with direct impact on people's lives, it's incredibly fulfilling!

One thing nobody has mentioned - be prepared for a LONG wait. I submitted my OIC in July last year with a very similar situation (living with non-married partner), and I'm still waiting for final determination. Got assigned an offer examiner in November who requested additional documentation, and I'm still in the "review" stage. The IRS is extremely backlogged right now. My examiner told me they're taking about 9-12 months on average to process OICs. So don't expect a quick resolution, even if you fill out everything perfectly.

I went through this exact situation about 18 months ago with my boyfriend of 3 years. The key thing to remember is that Form 433-A (OIC) is about YOUR financial reality, not your household's combined finances. Here's what I did and what worked for my successful OIC: **Income Section**: Only reported my own W-2 income and side gig earnings. Did NOT include my boyfriend's salary, even though we live together. **Expense Section**: This is where it gets tricky. I only reported the expenses I actually pay. For example: - Rent: We split it 50/50, so I only reported half - Utilities: He pays electric/gas, I pay internet/cable - so I only reported what I actually pay - Groceries: We alternate weeks, so I calculated my average monthly contribution **Assets**: Only included accounts and property in my name or jointly owned. His car, his savings account, etc. were not included. The IRS accepted my offer for $6,200 on a $38,000 debt. The key was being completely honest about what I actually pay vs. what the household pays total. Don't try to inflate your expenses by claiming full amounts when someone else covers part of them - the IRS will catch this if they audit your finances. One tip: Keep detailed records of how you split expenses. I had to provide this breakdown when my examiner asked for clarification during the review process.

This is a really comprehensive discussion, but I want to add one crucial point that could save you significant headaches: consider the timing of when you report your gambling income versus when you actually receive the funds in your US accounts. The IRS generally uses a cash basis for gambling winnings, meaning you report income when you actually receive it, not when you win it. So if you win €10,000 in December but don't transfer it to your US account until January, you'd typically report it in the following tax year. This can be useful for tax planning, especially if you're near year-end. However, this gets complicated with foreign currency. Some tax professionals argue you should report the income when won (using the exchange rate at that time), while others say you report when received in USD. The currency fluctuation between winning and receiving could create additional taxable events. Also, don't overlook state tax implications. Some states have no income tax, while others might tax your gambling winnings at high rates. If you're in a high-tax state, you might want to establish residency elsewhere before you start this venture - but make sure you do it properly to avoid dual-state tax issues. Given the complexity here, I'd strongly recommend getting a consultation with a tax professional who specializes in international gambling taxation before you start. The upfront cost could save you thousands in penalties and missed optimization opportunities.

One additional consideration that hasn't been fully addressed is the potential impact on your US banking relationships. Many major US banks have become increasingly cautious about customers who frequently move money to and from offshore gambling sites, even when it's perfectly legal. I've seen cases where banks have closed accounts or restricted services for customers engaged in offshore betting, not because of any legal issues, but due to their internal risk management policies. This is especially true if you're moving significant amounts regularly. Before you start, I'd recommend: 1. Notify your bank about your planned international transfers and gambling activity to avoid surprise account freezes 2. Consider maintaining relationships with multiple banks in case one decides they don't want your business 3. Look into banks that are more friendly to international transactions and gambling activities Some credit unions and smaller regional banks are more accommodating than the major nationals. Also, having a clear paper trail and being upfront about the source of funds goes a long way in maintaining good banking relationships. The last thing you want is to hit a big win only to have your bank account frozen while they investigate the source of a large international transfer. Planning ahead for the banking side can save you major headaches down the road.

Has anyone used the "zero out retained earnings" approach with TurboTax for their final S-Corp return? My accountant mentioned this but didn't explain how to actually do it in the software.

I went through this exact same situation when closing my S-Corp earlier this year. The balance sheet errors in TurboTax are usually caused by not properly accounting for where your cash went when you distributed it to yourself. Here's what worked for me: In TurboTax, you need to record that $4,200 as a "Distribution to Shareholders" under the equity section, not as an expense. This creates the proper offsetting entry that balances your books - cash goes down by $4,200, and shareholder equity (retained earnings) also goes down by $4,200. For the disposed assets, since you mentioned they were old equipment, make sure you're removing both the original cost AND the accumulated depreciation from your books. If they were fully depreciated, this should net to zero impact. One thing that caught me off guard - make sure your final balance sheet shows zero equity at year-end if you're completely liquidating. All retained earnings need to be distributed out to shareholders for the books to properly reflect a dissolved corporation. The IRS has specific requirements for S-Corp dissolution, so double-check that you're filing Form 966 in addition to your final 1120-S return. Good luck with the closure!