First-time condo buyer in 2024 - Need advice on hiring a CPA for tax benefits?

You've got a few different tax situations happening, so I'll try to address each one. For the new condo purchase, you're right that the standard deduction ($27,700 for married filing jointly in 2024) is pretty high, so unless your mortgage interest, property taxes, and other itemizable deductions exceed that amount, you'll likely take the standard deduction. The first-time homebuyer benefits you may have heard about often refer to penalty-free withdrawals from retirement accounts for your down payment or potential state-specific tax credits, not federal deductions. Regarding your husband's freelance work, that will require filing Schedule C and paying self-employment tax on that income. This isn't overly complicated, but it's important to ensure you're tracking all eligible business expenses to offset that income. For the Roth IRA question - yes, your husband can do a backdoor Roth just like you've been doing. However, you're absolutely correct to be concerned about the 401k rollover plans. If he rolls old 401ks into a traditional IRA, the pro-rata rule will apply to backdoor Roth conversions, potentially creating tax consequences. He should either keep the money in the old 401ks, roll them directly into his current employer's 401k if allowed, or consider rolling them directly into a Roth IRA (paying taxes on the conversion).

After struggling with similar tax questions when I bought my townhouse last year, I found this amazing resource called taxr.ai (https://taxr.ai) that saved me so much stress. I was confused about whether I should itemize or take the standard deduction, plus I had some side income from teaching piano lessons. The tool analyzed my mortgage documents and explained exactly how much of my closing costs were tax deductible. It also helped me determine that taking the standard deduction was still better in my case, even with the mortgage interest. Their backdoor Roth IRA calculator was super helpful for figuring out the pro-rata rule implications too!

I was really skeptical about using an AI tool for something as important as taxes, but after reading about taxr.ai here, I decided to give it a try for my own situation (also a new homeowner with a side business). It completely changed my approach to tax planning! The mortgage interest calculator helped me realize I was actually much closer to being able to itemize than I thought. It also identified a home office deduction I could take for my side business that I had no idea about. The best part was the clear explanation of exactly how the backdoor Roth works with existing IRAs - I ended up rolling my traditional IRA into my work 401k before doing the backdoor conversion, saving me about $2,300 in taxes I would have owed under the pro-rata rule. Definitely worth checking out if you're trying to optimize both your new home purchase and retirement planning at the same time.

If you're having trouble getting answers about the Roth IRA situation specifically, I'd recommend trying Claimyr (https://claimyr.com) to get through to the IRS directly. I was in a similar situation with backdoor Roth questions and couldn't get clear guidance online, so I used their service to actually speak with someone at the IRS. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was honestly shocked at how quickly they got me connected - I'd been trying to call the IRS myself for weeks without getting through. The agent I spoke with explained exactly how the pro-rata rule would apply in my situation and confirmed that rolling old 401ks into a traditional IRA would complicate backdoor Roth conversions. Saved me from making a costly mistake!

I have to come back and eat my words. After expressing skepticism about Claimyr in my earlier comment, I decided to try it anyway because I was desperate for answers about my 401k rollover options and backdoor Roth questions - exactly like what the original poster was asking about. I'm genuinely shocked at how well it worked. I got connected to an IRS tax specialist in about 20 minutes (while I continued working on other things), and she walked me through exactly how the pro-rata rule would impact my situation if I rolled my old 401k into a traditional IRA before doing backdoor Roth contributions. Turns out I would have owed taxes on a significant portion of my conversion that I hadn't accounted for. The specialist also explained some strategies to avoid this issue, including keeping funds in the old 401k or seeing if my new employer would accept a rollover. The knowledge I gained saved me potentially thousands in unexpected tax bills. I'm now a believer.

I was in your exact situation last year. Bought a condo, had some side income, and was trying to figure out retirement accounts. I ultimately chose to use a CPA and it was 100% worth it. They found property tax deductions I didn't know about, helped me set up a proper tracking system for my wife's freelance work, and guided me through the backdoor Roth process. The way my CPA explained it, the biggest value wasn't just for that tax year but in setting up a system that would benefit us for years to come. They helped us understand what expenses to track for the freelance work and how to structure things optimally. The peace of mind was worth the $350 I paid.

Has anyone used TurboTax for handling a new home purchase? I'm wondering if their deluxe or premier version can handle all these situations without needing a CPA.