4 Has anyone used TurboTax or similar software for filing back taxes? Or do you need to go through a tax professional? I'm in a similar situation (missing 2019-2020) and trying to figure out the cheapest way to get caught up.

I'm in a very similar boat - didn't file 2018-2020 and just got caught up on recent years. One thing I learned that might help you: if your income was under the filing threshold for those years (around $12,200 for single filers in 2017-2019), you technically weren't required to file. But even if that's the case, filing can still be beneficial. Here's what I'd recommend: start by requesting your wage and income transcripts from the IRS for those years to see exactly what income was reported. This will help you determine if you actually owe anything or if you might be due refunds you didn't expect. For your financial aid situation, while FAFSA mainly looks at the prior-prior year, some schools do ask for additional tax information during verification. Having everything filed removes any potential roadblocks there. The peace of mind factor is huge too. I was constantly worried about getting a letter from the IRS, and filing those back years eliminated that stress completely. Even if your tax guy thinks it's unnecessary, it's your call - and honestly, a good tax professional should support getting you fully compliant rather than questioning it.

Don't overthink this! I formed my LLC 2 years before I made a single dollar. Just keep your business and personal finances separate from day one (separate bank account is a must), track all expenses meticulously, and save receipts for everything. For accounting software, check out Wave - it's completely free for basic accounting and receipt tracking. You can connect your business bank account and it'll pull in all transactions automatically. When you start making money, I'd recommend getting professional help around the $5k revenue mark. Before that, most accountants will charge you more than they're saving you.

I'll add another perspective as someone who went through this exact situation with my SaaS startup. You're absolutely right to form the LLC before launching - it's completely legal and actually smart business planning. One thing I wish I'd known earlier: consider getting an EIN (Employer Identification Number) from the IRS as soon as you form your LLC, even before you have revenue. It's free, takes about 15 minutes online, and you'll need it to open your business bank account anyway. Having the EIN also means you won't have to use your SSN for business purposes, which adds another layer of personal protection. For your subscription model specifically, make sure you understand the difference between cash and accrual accounting methods. Since you'll likely be collecting monthly payments, this could affect when you report income for tax purposes. Most small businesses can use cash accounting (report income when received), but it's worth confirming with a professional once you start generating revenue. Also, don't forget to check if your city or county requires a business license for your type of service. This is separate from the LLC formation and varies widely by location and business type. Some areas require it before you start operating, even in the pre-revenue phase. You're taking the right approach by planning to bring in professional help once you have steady income. Just make sure you're documenting everything from day one - it'll save you money when you do hire that accountant!

This thread has been incredibly informative! I'm a freelance graphic designer who regularly meets clients for coffee and lunch meetings, and I've been making some mistakes with my deductions. One thing I'm still unclear on: what about meals during networking events? I attend monthly chamber of commerce meetings that include lunch, and I often meet potential clients there. The lunch is included in the registration fee - should I be tracking that separately as a 50% deductible business meal, or is it part of the overall networking event cost? Also, for those using expense tracking apps or services, do you find they handle mixed situations well? Like when you take a client to lunch (50% deductible meal) but also give them promotional materials or small gifts during the meeting - I assume those would be tracked differently for tax purposes? Really appreciate everyone sharing their experiences here. It's so much more helpful than trying to decode IRS publications on my own!

This has been such a helpful thread! I'm a small business owner who's been struggling with these exact distinctions. One area I'm still confused about is meals during business travel that involve entertainment components. For example, last month I took a potential client to dinner while I was traveling for business, and afterwards we went to a comedy show to continue our discussion. I know the dinner should be 50% deductible as a business meal, but what about the comedy show tickets? Since we did discuss business during the show (between acts), would any portion of that be deductible, or is it completely non-deductible as entertainment? Also, I've been tracking my expenses manually in spreadsheets, but after reading about the tools mentioned here, I'm wondering if I should upgrade my system. Has anyone compared different expense tracking solutions specifically for handling these meal vs entertainment distinctions? I want to make sure I'm not leaving money on the table or setting myself up for audit issues. The documentation tips shared here are gold - I definitely need to get better at recording the business purpose and attendees for each expense. Thank you all for sharing your experiences!

One thing that hasn't been mentioned yet is state residency vs. federal residency. You might be considered a resident alien for federal tax purposes but a nonresident for state tax purposes (or vice versa). Some states have completely different rules!

Based on your detailed travel history, you'll likely be considered a resident alien for 2025 tax purposes under the Substantial Presence Test. Here's a quick calculation: **2025 days**: You've been here since January 1st (let's say ~90 days so far) **2024 days**: From your dates, approximately 348 days × 1/3 = 116 days **2023 days**: From your dates, approximately 335 days × 1/6 = 56 days Total: ~262 days, which exceeds the 183-day threshold. However, don't overlook the **closer connection exception** you mentioned. Since you maintain bank accounts and property in your home country, you might qualify. You'd need to file Form 8840 to claim this exception and prove that despite being physically present in the US, your tax home and closer connections remain with your home country. Key factors the IRS considers for closer connection: - Where your permanent home is located - Your family and social ties - Your business activities and professional affiliations - Where you vote and hold driver's licenses - Which country you designate as residence on official forms I'd strongly recommend consulting with a tax professional who specializes in international tax law, as this determination can significantly impact your tax obligations and filing requirements for 2025.

One crucial aspect that hasn't been fully addressed is the timing and documentation for your Korean tax residency. Since you're planning to stay 2-3 years, you'll likely become a Korean tax resident after 183 days in a calendar year, which means you'll need to file Korean tax returns on your worldwide income. However, there's a specific provision in the US-Korea tax treaty (Article 15) that may allow your employment income to remain taxable only in the US if certain conditions are met - mainly that your employer has no permanent establishment in Korea and you're not performing services that create one. This is where the permanent establishment analysis mentioned earlier becomes critical. I'd also recommend checking if your current employer has any existing policies about international remote work. Many companies have blanket policies prohibiting it due to the complexity, but some have frameworks already in place. If they don't, presenting them with a comprehensive compliance plan (including the EOR option, tax analysis, and permanent establishment mitigation strategies) will show you've done your homework and make approval more likely. Finally, consider the practical aspects - time zone differences with your team, internet reliability for video calls, and whether your role requires access to any US-specific systems or data that might have geographic restrictions.

One additional consideration that could significantly impact your situation is Social Security and Medicare taxes. As a W-2 employee working abroad, you'll still owe US Social Security and Medicare taxes (FICA) on your income, and your employer will still need to pay their portion. This is different from self-employment tax if you were to go the 1099 route. However, there's a potential benefit here - the US has a Social Security Totalization Agreement with South Korea. This means that if you end up paying into the Korean National Pension System (which is mandatory for most workers), you may be able to get credit for those contributions toward your US Social Security benefits, and vice versa. You'll need to file Form SSA-21 to claim these benefits later. Also, make sure you understand the implications for your future immigration plans. If you're planning to sponsor your spouse for a US visa down the road, maintaining continuous US employment and tax filing can actually strengthen that application by demonstrating ongoing ties to the US and ability to financially support them. One practical tip: set up a VPN through your employer if possible, as many US banking and financial websites will block access from foreign IP addresses, which can make managing your US financial obligations quite difficult otherwise.