This is super helpful! Can I ask roughly what you paid for each type of professional? And did you notice a big difference in the amount of tax savings as you "upgraded" to more specialized help?

For the bookkeeper and tax preparer combo, I paid about $80/month for bookkeeping and $350 for tax preparation, so roughly $1,310 annually. They mainly just organized things and filed correctly, but didn't offer much strategic advice. The Enrolled Agent/tax consultant cost me about $1,800 annually but found an additional $4,200 in deductions the first year - home office, mileage, and several business expenses I didn't realize were deductible. Definitely a worthwhile upgrade. My CPA costs about $3,200 annually but has structured my business to save approximately $11,000 in taxes through strategic planning, retirement contributions, and helping me choose the right business entity. As your business grows more complex, the potential tax savings generally increase enough to justify the higher fees.

How do you handle quarterly estimated tax payments with this approach? That's the part I find most confusing with my side business.

Thanks for pointing that out. The agreement we have is more like a promissory note with the house as collateral. We knew we weren't on the deed, and trusted her (plus had the signed agreement). But you're right that in a worst-case scenario, we'd have had to take legal action if she refused to pay. For future reference, would you recommend actually getting on the deed for this kind of arrangement? Or is there a better way to structure it?

For future reference, there are several better ways to structure this. If you want actual ownership, you absolutely need to be on the deed - that's the only thing that legally establishes property ownership. Your name on the deed would make you true partial owners. If you prefer the loan approach (which is simpler), you could use a recorded mortgage or deed of trust. This creates a public record of your loan against the property and gives you much stronger legal protection. If she didn't repay, you'd have a straightforward foreclosure process rather than having to sue based on a private agreement. Either way, for amounts this large, it's worth spending a few hundred dollars on a real estate attorney to structure it properly. The peace of mind and legal protection are absolutely worth it.

This is so frustrating! The government makes you report large deposits of YOUR OWN MONEY coming back to you? It's none of their business if my family pays me back money I lent them. The whole banking system is designed to treat everyone like criminals.

Thanks for the tip about Form 1096! I wasn't aware I needed to file that as well. Is there a deadline for submitting that form that's different from my regular tax filing?

The deadline for filing Form 1096 along with all your 1099-NEC forms to the IRS is January 31, 2026 for the 2025 tax year. This is earlier than your personal tax return deadline (April 15) because the IRS needs time to process these forms and match them against what contractors report on their returns. If you've already sent 1099-NECs to the government as you mentioned, hopefully you included the 1096 with them. If not, you should file it as soon as possible even if it's late. The penalties for late filing start at $50 per form if you're less than 30 days late, and increase the longer you wait.

TurboTax does a decent job with Schedule C. It asks you questions about your business expenses and suggests categories based on your answers. For contractor payments, it specifically asks if you paid independent contractors and guides you to put those on Line 11. It also reminds you about 1099 requirements. I found it pretty helpful for basic Schedule C stuff, but for more complex situations like deciding if something is truly "advertising" versus another category, you might still need to do some research on your own.

Thanks for the info! That's reassuring to hear that TurboTax guides you through the contractor payments part. I'll give it a try this year instead of stressing about categorizing everything perfectly beforehand.

11 What kind of tax treaty benefits did you find with the UK? My wife is from Canada and I'm wondering if there are similar advantages. Also, what's the threshold for FBAR reporting? We have a joint account in her country but it's not a huge amount.

3 The UK-US tax treaty had specific provisions about pension contributions and certain types of investment income that were beneficial in our case. Every treaty is different though - the US-Canada one has its own unique aspects, so definitely look into that specifically. For FBAR reporting, the threshold is if your foreign accounts combined exceed $10,000 at any point during the year. Even if your individual account is small, if you have multiple accounts that together exceed that amount, you need to file. And remember, it's not just bank accounts but also investment accounts, certain pension accounts, etc.

13 I e-filed last year with my husband's ITIN. The trick is that you need to enter the ITIN exactly as it appears on the ITIN letter from the IRS, including any hyphens. I had problems at first because I was entering it without hyphens.

Thanks for this tip! How long does it typically take for transcripts to become available after e-filing? Is it something I can access immediately after getting the acceptance confirmation?

Transcripts are usually available within 2-3 weeks after your e-filed return is accepted, sometimes even faster. You won't have access immediately after acceptance - the IRS needs to do some initial processing first. You can request them through the "Get Transcript" tool on IRS.gov once they're available. If you set up an online account with the IRS in advance, you'll be ready to download them the moment they're processed. Some mortgage lenders can also request the transcripts directly through a service called 4506-T if you sign an authorization form, which might save you some time.

I tried this route last year. You need to make an appointment first by calling 844-545-5640. They won't just let you walk in anymore. When I went, they helped me fill out the forms but still had to submit them through regular channels. They did give me a stamped copy though which my lender accepted as proof of filing.