I completely understand your concerns - those communication issues alone would make me uncomfortable, regardless of whether it's an actual scam. Poor communication from a professional handling your sensitive financial information is never acceptable, busy season or not. Here's what I'd suggest doing immediately: First, request copies of all documents they used to prepare your return and a detailed explanation of their work. Any legitimate CPA should provide this without hesitation. Second, consider having another tax professional review your return - many will do a quick review for a reasonable fee to spot obvious errors or missed opportunities. Regarding the spam increase, while it could be coincidental, it's worth monitoring your credit reports closely. You can get free reports from annualcreditreport.com to check for any suspicious activity. The fact that they dismissed your questions about deductions without proper explanation is particularly concerning. A good CPA should educate their clients, not brush them off. Even if those deductions truly didn't apply, they owe you a clear explanation of why. Moving forward, I'd recommend finding a new tax preparer for next year. Look for someone who offers transparent communication, provides detailed explanations, and comes with strong references from people whose tax situations are similar to yours.

I went through something very similar last year and want to share what I learned. The communication issues you're describing are unfortunately common but definitely not acceptable - a professional CPA should have systems in place to manage client communication even during busy season. What really helped me was documenting everything. I started keeping a log of every email sent, phone call made, and response (or lack thereof) received. This gave me a clear picture of the communication breakdown and also served as evidence when I eventually had to escalate the situation. For the deduction issues, I'd strongly recommend getting a second set of eyes on your return. I paid another CPA $150 to review my completed return, and they found two legitimate deductions my original preparer had missed, plus confirmed that several categorizations were questionable. The review fee was worth it for the peace of mind alone. The spam increase is concerning - while it could be coincidental timing with tax season, it's worth placing fraud alerts on your credit reports just to be safe. I did this as a precaution and it only takes a few minutes online. Moving forward, I'd suggest requesting a detailed meeting to go over every decision they made on your return. If they can't or won't provide clear explanations, that's your answer about whether to continue working with them. A legitimate CPA should welcome the opportunity to educate their clients about tax decisions.

I went through this exact same situation a couple years ago! The stress is real, but here's what I learned after consulting with a tax professional: Since these "thank you" payments are directly tied to your babysitting services, they're almost certainly considered tips/additional compensation rather than gifts. The IRS doesn't care what the family calls them - what matters is that they're given in appreciation of services you provided. You should report all of these payments as income, even if you don't receive a 1099. Keep track of everything - screenshots of Venmo transactions, notes about cash payments, etc. If it totals over $400 for the year, you'll also need to file Schedule SE for self-employment tax. One tip: start keeping better records now for next year. Create a simple spreadsheet tracking your regular pay vs. these bonus payments. It'll make tax time much less stressful! And don't panic - the IRS is generally understanding if you're making a good faith effort to report everything correctly.

Hey Oliver! I totally understand the stress - I was in almost the exact same boat last year with irregular payments from a tutoring family. The uncertainty about whether you're doing something wrong is the worst part! Based on everything I learned (and what others have shared here), those Venmo "thank you" payments are almost definitely going to be considered income since they're directly tied to your babysitting work. Even though they're irregular and the family is calling them gifts, the IRS looks at the underlying reason for the payment. A few practical things that helped me: - Start tracking everything NOW in a simple spreadsheet (regular pay vs bonus payments) - Take screenshots of all your Venmo transactions - Keep notes about any cash payments with dates and amounts - Don't wait until tax season to figure this out The good news is that even if you owe some extra taxes (including self-employment tax if it's over $400 total), you're not going to get in serious trouble for making a good faith effort to report everything correctly. The IRS really goes after people who are intentionally hiding income, not folks like you who are actively trying to do the right thing. You've got this! Better to deal with it now than stress about it for months.

Has anyone considered the step-up in basis implications here? If the house appreciates and you both own it, when one spouse dies, the surviving spouse might only get a step-up in basis on half the property value. Whereas if only one spouse owns it, the entire property could get a step-up when that spouse dies. Just something to think about for long-term planning.

You're absolutely right about the step-up in basis considerations, and @Victoria Scott brings up an excellent point about non-citizen spouses and estate tax rules. For estate tax purposes, the unlimited marital deduction that applies to citizen spouses does NOT apply to non-citizen spouses, even if they're permanent residents. Instead, there's a much lower annual exclusion (around $185,000 for 2024). This means that when a US citizen dies, transfers to a non-citizen spouse above this threshold could be subject to estate tax. However, there's a planning tool called a Qualified Domestic Trust (QDOT) that can help defer estate taxes for non-citizen spouses. The surviving non-citizen spouse can receive income from the trust, and estate taxes are deferred until distributions of principal or until the surviving spouse becomes a US citizen. So while adding your wife to the deed now creates the gift tax filing requirement we've discussed, it might actually be beneficial from an estate planning perspective since it gets half the property out of your taxable estate. But this is definitely getting into complex territory where you'd want to consult with an estate planning attorney who understands the international implications. The basis step-up issue is real though - with joint ownership, only half the property gets a stepped-up basis when the first spouse dies, versus the full step-up if only one spouse owned it.

Great question about the home office deduction! Yes, you can absolutely still claim the home office deduction after marriage when filing jointly, as long as you meet the IRS requirements. The key is that the space must be used "regularly and exclusively" for business purposes - meaning it's your dedicated workspace and not used for personal activities like watching TV or as a guest bedroom. You have two options for calculating the deduction: the simplified method (up to $5 per square foot, max 300 sq ft = $1,500 max deduction) or the actual expense method where you calculate the percentage of your home used for business and deduct that percentage of qualifying home expenses like utilities, insurance, repairs, etc. Since your business is breaking even now, maximizing these deductions becomes even more important for reducing your self-employment tax liability. Keep detailed records of your home office measurements and any business-related expenses. When you file jointly, this deduction will help offset your self-employment income regardless of your spouse's W-2 income.

One additional consideration that hasn't been mentioned yet - when you get married, your filing status changes for the ENTIRE tax year, even if you only get married on December 31st. So if you're getting married this fall, you'll need to decide on your filing status for the full 2024 tax year. This means you should start planning now for how marriage will affect your quarterly estimated payments for the rest of the year. If filing jointly will result in tax savings (which it sounds like it will based on the other responses), you might be able to reduce your remaining quarterly payments slightly. Also, once you're married, you can choose to make joint estimated tax payments rather than separate ones, which can simplify the process. Just make sure to recalculate your estimates based on your combined income and the filing status you plan to use. Given your income levels and his dependent child, I'd strongly recommend running the numbers both ways before your wedding so you can adjust your tax withholding and estimated payments accordingly for Q4.

This thread has been absolutely fantastic for understanding the practical side of running multiple sole proprietorship businesses! I'm currently operating a small home-based bakery and I'm looking to expand into catering services. Reading through everyone's detailed experiences has really clarified that I can use my existing EIN for both food-related businesses. The consistent advice about separate bank accounts, detailed record keeping, and proper quarterly tax planning is exactly what I needed to hear. I'm particularly grateful for the insights about DBAs - it makes total sense that "Sweet Treats Bakery" and "Sweet Treats Catering" would feel more professional to clients than just using my personal name for both. One food-specific question I have: since both businesses involve food preparation but catering requires additional permits and health department oversight compared to my home bakery license, has anyone dealt with how different regulatory requirements interact with the single EIN setup? I assume the permits are separate from the tax ID, but I want to make sure there aren't any complications I'm missing. Also, the insurance discussion has been really eye-opening. I'll definitely need to look into whether my current home bakery coverage can extend to catering events, or if I'll need additional liability coverage for off-site food service. Thanks to everyone who shared such comprehensive, real-world advice - this is exactly the kind of practical guidance that's impossible to find in official tax documents!

This has been such an educational thread! I'm in the process of expanding from my existing freelance writing business to add social media management services, and all of these real-world experiences have been incredibly helpful in understanding how to structure things properly. The consistent theme about organization being key really resonates with me - separate bank accounts, detailed record keeping, and proper quarterly tax planning seem to be non-negotiable for success with multiple businesses under one EIN. I'm definitely planning to set up a second business account before I even start taking on social media clients. The DBA discussion has been particularly valuable. While my writing clients know me as "Sarah Chen Copywriting," it makes sense to establish "Sarah Chen Social Media" as a distinct brand for the new service line, even though both will use the same EIN behind the scenes. One question I have that's specific to service-based businesses: for those offering different types of professional services, have you found that clients sometimes expect different contract terms or payment schedules between business types? I'm wondering if having distinct business identities through DBAs helps manage these different client expectations, or if you've found ways to standardize processes across multiple service offerings. The insurance insights have also been really helpful - I'll need to review whether my current professional liability coverage adequately addresses both writing and social media management, since they involve different types of client deliverables and potential risks. Thanks to everyone for sharing such detailed, practical experiences!