Sophia, this is such an inspiring discussion to read! Your thoughtful approach and genuine desire to help people really comes through. As someone who's worked in financial services, I can tell you that having that combination of technical knowledge (bookkeeping degree, math skills) and personal understanding (doing family taxes, immigrant background) is incredibly valuable. One thing that struck me is how this thread has showcased the evolution of the tax industry - from traditional preparation to AI-assisted tools like taxr.ai for accuracy, to services like Claimyr for IRS communication efficiency. As a newcomer, you're actually entering at a great time when technology can amplify your skills rather than replace them. I love the suggestions about the VITA program for hands-on training and potentially specializing in immigrant communities. That specialization could really set you apart, especially if you can combine it with modern efficiency tools. The seasonal nature that others mentioned is definitely something to plan for, but it sounds like you're approaching this thoughtfully rather than jumping in blindly. Your bookkeeping background will definitely help with the business side - understanding cash flow patterns, organizing client data, and maintaining professional standards. Best of luck with whatever you decide! This community seems to have given you some excellent guidance to help make an informed choice.

Reading through this entire thread has been absolutely fascinating! As someone who's been considering various side hustles, I'm impressed by how thorough and supportive this community is. @Sophia Rodriguez - your journey from considering tax preparation to having a clear roadmap is really inspiring. The combination of your bookkeeping background, family tax experience, and genuine desire to help people (especially immigrant families) seems like such a strong foundation. What strikes me most about this discussion is how it's evolved from basic viability questions to covering everything from certification paths (VITA program, EA certification) to modern technology tools (taxr.ai for accuracy, Claimyr for IRS efficiency) to specialization strategies. It really shows how much the tax preparation field has to offer for someone willing to approach it professionally. The seasonal nature and intensity seem manageable as a side hustle, especially with the potential for year-round client relationships through tax planning services. And the emphasis on proper insurance, business setup, and starting with supervised experience through VITA shows there's a clear path to do this right. This thread is a perfect example of how valuable community knowledge-sharing can be. Thanks to everyone who contributed their experiences and expertise!

I'm dealing with a similar phone verification issue and wanted to share what worked for me. After weeks of frustration, I called the IRS Practitioner Priority Service line (even though I'm not a practitioner) and explained I was an international filer with account access issues. The agent was able to manually verify my identity using my previous tax returns and reset my account access without requiring phone verification. The key was having my Social Security card, previous year's tax return, and a utility bill ready when I called. The wait time was about 45 minutes, but it saved me from waiting weeks for mail delivery overseas. You might also want to try accessing your account early in the morning (around 6-7 AM EST) when the system load is lighter - I've noticed fewer verification errors during off-peak hours.

I've been through this exact nightmare! The phone verification system is absolutely broken for international filers. Here's what finally worked for me after 3 weeks of trying everything: 1. **Call the International Taxpayer Services line at (267) 941-1000** - they're specifically trained for overseas filing issues and can actually override the phone verification requirement. Best calling times are 6-8 AM EST. 2. **Have these documents ready**: SSN card, last year's return with exact AGI and refund amounts, and any documentation showing your current international address. 3. **Don't create a new ID.me account** - this will just create more problems in their system. The agents can reset your existing account once they verify your identity manually. 4. **Request a "manual account unlock"** specifically - use those exact words. This puts you in a different queue that bypasses the automated phone verification. The whole process took about 2 hours on the phone, but I got immediate access to my transcripts afterward. Much better than waiting weeks for mail delivery overseas. The agent also flagged my account so future logins won't require phone verification. Hope this helps - the international taxpayer line is definitely your best bet!

That price seems high but not crazy depending on where you live. I'm in NYC and was quoted $3200 for a similar situation (W-2 plus freelance plus a rental condo). I ended up using H&R Block Premium and it handled everything fine. Just make sure to keep REALLY good records of your rental expenses and freelance costs. The software walks you through everything. The biggest issue with rental property is properly calculating depreciation and understanding what expenses can be deducted vs capitalized. If you research those topics specifically, the rest is pretty straightforward in most software packages.

That quote does seem excessive! I'm a tax preparer myself, and while rental property plus freelance income does add complexity, $2700 is on the very high end unless you have some unusual circumstances they didn't mention. Here's what I'd suggest: Get at least 2-3 more quotes from different types of tax professionals - CPAs, enrolled agents, and even some of the larger chains like H&R Block. Prices can vary wildly even for the same work. That said, given your comfort level with TurboTax in the past, you might be surprised how well the premium versions handle rental properties now. TurboTax Premier or H&R Block Premium can walk you through Schedule E for rental income and Schedule C for freelance work. The key is having organized records and taking your time. One middle-ground option: prepare your return using software first, then pay a CPA just to review it before filing. This usually costs $200-400 but gives you professional oversight without the full preparation fee. Many CPAs offer this service and it might give you peace of mind for your first year with the rental property.

I went through this exact situation when my mother passed away last year, and I completely understand how overwhelming it can be. Here are a few additional points that might help: Since your father passed in September 2022, you're right that his final Form 1040 is due April 15, 2023. Don't forget you can write "DECEASED" after his name and the date of death on the return. You'll sign as the personal representative. For the trust, one thing that caught me off guard was needing to file Form 56 (Notice Concerning Fiduciary Relationship) with the IRS to officially notify them of your role as executor. This should be done fairly early in the process. Also, even though you're selling in 2023, consider whether any expenses related to maintaining or preparing the house for sale in 2022 after your father's death might be deductible on the trust's 2022 return (Form 1041). Sometimes there are small amounts of income or deductible expenses even when you think there's nothing to report. The step-up in basis mentioned by Emily is huge - make sure you have good documentation of the property's fair market value as of your father's date of death. This could save you significant capital gains tax when you sell. Hang in there - it does get easier once you understand the process!

As someone who recently went through this exact process as an executor, I wanted to add a few practical tips that really helped me stay organized: First, create a dedicated checking account for the trust if you haven't already. This makes tracking all trust-related income and expenses much cleaner for tax reporting. When you sell the house, having all the proceeds flow through the trust account creates a clear paper trail. Second, keep meticulous records of ALL expenses related to the property from the date of death forward. This includes utilities, insurance, property taxes, maintenance, realtor fees, staging costs, repairs, etc. Many of these are deductible against the sale proceeds and can significantly reduce the trust's taxable gain. Regarding timing - don't wait until the last minute to start preparing the 1041. The form is more complex than a typical 1040, and if you're distributing proceeds to multiple beneficiaries, you'll need to prepare K-1s for each of them. They'll need those K-1s to file their own returns, so getting this done early helps everyone. One last thing - if the sale happens late in 2023, consider whether it makes sense to distribute the proceeds to beneficiaries before year-end. If they're in lower tax brackets than the trust's compressed tax rates, this could save the family money overall. The trust tax brackets are much more compressed than individual rates, so trusts hit higher rates quickly. You're doing great navigating this complex process - it's a lot to handle but you'll get through it!

I'm in a similar situation as a freelance tutor and had the same panic about tax filing! You absolutely can report your income without a 1099-NEC. I used my bank statements showing the Zelle deposits and created a simple spreadsheet tracking the dates and amounts. The key thing is to keep good records going forward. I started screenshotting every payment notification and keeping them in a folder on my phone. Also, don't feel bad about not discussing this earlier with your employer family - most people don't realize the tax implications of household help until it's time to file. One tip: if you do end up owing a significant amount, you can set up a payment plan with the IRS. It's way less stressful than trying to come up with everything at once!

Don't stress too much about this! You're absolutely doing the right thing by wanting to report your income properly. As others have mentioned, you can definitely report your nanny earnings without a 1099-NEC. Since you're paid through Zelle, you actually have a great digital trail of your income. Here's what I'd recommend: Go through your Zelle history and add up all payments from this family for the tax year. Report this total on Schedule C as self-employment income. Yes, you'll pay the higher self-employment tax rate, but it's better than not reporting it at all. Regarding your question about paying penalties if your employer family files a late 1099-NEC - honestly, that's their responsibility as the employer, not yours. You brought it up as soon as you realized the situation, and you're taking steps to report your income correctly. Don't feel like you need to cover their potential penalties. For next year, definitely have the tax conversation earlier in your working relationship. Many families genuinely don't know about the "nanny tax" rules, so it's often up to us to educate them about proper reporting and documentation.