Late to the party but another option: calculate your taxes ALL THREE WAYS! Run the numbers as: 1. Married filing jointly 2. Married filing separately 3. As if you were both still single (for comparison) This will show you the exact marriage penalty/bonus in your situation. My wife and I have similar incomes to you guys ($170k and $135k) and we found filing jointly saved us about $3,800 compared to separate even though we have the "penalty" compared to when we were single. Tax software makes this pretty easy to model different scenarios.

Great advice from everyone here! As someone who went through this exact situation two years ago (similar incomes, newly married), I can confirm that running the calculations both ways is absolutely worth it. One thing I'd add that hasn't been mentioned much - don't forget about retirement account contribution limits if you're both maxing out 401(k)s. The income limits for IRA deductibility change when you're married filing jointly, and with your combined income around $320k, you might lose the ability to deduct traditional IRA contributions that you could make when single. Also, if either of you contributes to an HSA, those limits and eligibility rules can change too. We ended up saving about $4,200 by filing jointly despite losing some deductions we had when single. The higher standard deduction and avoiding the loss of various credits made joint filing the clear winner for us. Definitely echo the suggestion to use tax software to model both scenarios - seeing the actual dollar difference makes the decision much easier than trying to figure it out theoretically!

Don't forget that even though you filed an extension, you still need to submit your return by October 15th to avoid late filing penalties! Extension season always goes by faster than people expect.

Just wanted to chime in with my experience - I switched from TurboTax to FreeTaxUSA after filing an extension and it worked perfectly! The key thing to remember is that your extension (Form 4868) is completely separate from your actual tax return filing method. I was in a similar boat with TurboTax trying to charge me $89 for federal plus state fees. FreeTaxUSA ended up costing me only $15 for state filing (federal was completely free) and walked me through everything step by step. The interface isn't as fancy as TurboTax but it gets the job done and their support was actually more helpful when I had questions. One tip: make sure you have all your documents organized before you start with any new service since you'll be entering everything fresh. Also double-check that any estimated tax payments you made with your extension are properly reflected in the payments section of your return. Good luck!

def check ur bank statements for those dates. sometimes they come from different names not just 'IRS

I went through something similar last year with missing Child Tax Credit payments. Here's what worked for me: First, call the IRS Child Tax Credit Update Portal helpline (not the main number) - it's usually less busy. Second, gather ALL your bank statements for July-December 2021 and check for deposits from "IRS TREAS" or "US TREASURY" - sometimes they don't show as "IRS". Third, if you truly didn't receive them, you'll need to file Form 8812 with your 2021 return to claim the missing credits. The IRS has been dealing with tons of these cases since the advance payments started, so they have a process for it. Just be prepared with documentation showing you never received the payments when you call!

I went through this exact same situation two years ago! You definitely need to pay quarterly taxes on that income even without the LLC formed yet. The IRS doesn't care about your business structure - they care about the income you're earning. With $3,500 so far this year, you're likely looking at owing around $500-700 in self-employment tax alone (that's the Social Security/Medicare tax at 15.3%), plus regular income tax on top of that. If you expect to make more throughout the year, you could easily hit that $1,000 threshold that triggers the quarterly payment requirement. My advice: don't wait until you form the LLC. Calculate your estimated taxes now using Form 1040-ES and make the payment. You can always adjust future quarters once your LLC is formed. The penalties for underpayment can be way more expensive than just paying a bit extra now to be safe. Also, keep those spreadsheets organized! You'll need them for Schedule C when you file, whether you're still a sole proprietor or have formed the LLC by then.

Great question! As someone who's helped many clients through this transition, I want to clarify a few key points that might save you some headaches. First, regarding the $500-700 self-employment tax estimate - that would be roughly what you'd owe for the full year if you only made $3,500 total. But since you're asking about quarterly payments, you need to project your full-year income. If you think you'll make $10,000+ this year, you're looking at significantly higher tax obligations. For quarterly payments, you should estimate your total annual business income, then pay 25% of your expected annual tax liability each quarter. Don't just base it on what you've earned so far - the IRS wants you to pay as you earn throughout the year. Regarding the LLC transition mid-year: it's actually pretty seamless for tax purposes. You'll report all your business income for the entire year on Schedule C, whether it was earned as a sole proprietor or after LLC formation. The LLC formation date doesn't create a tax filing break - it's all one continuous business year on your personal return. One tip: if you're unsure about your projections, it's often safer to pay a bit more in estimated taxes rather than underpay. You'll get any overpayment back as a refund, but underpayment penalties can be costly and annoying to deal with.

Does anyone know if I can still do this recharacterization thing for my 2024 contribution? I contributed to a Roth earlier this year but just realized my income will be too high.

Just wanted to add another perspective on this situation. I had a very similar mess with my 2023 Roth contribution and recharacterization timing, and what really helped me was understanding that the IRS treats the recharacterization as if you had made the correct choice from the beginning. The key insight that wasn't immediately obvious to me: when you recharacterize in 2024 for a 2023 contribution, you're not making a new 2024 contribution - you're retroactively changing what type of contribution you made in 2023. This is why your 2024 Roth contribution is completely separate and valid. Make sure when you're entering the 1099-R information in your tax software that you're categorizing it correctly. The recharacterization 1099-R should be coded as "N" and the conversion should be coded as "2". If your software is still showing over-contribution after entering these correctly, you may need to manually override the calculation or seek help from a tax professional who understands backdoor Roth conversions. Also double-check that your custodian reported everything with the correct tax year designations on the 1099-Rs. Sometimes they get confused about which year a recharacterized contribution should be attributed to.