As a fellow freelancer who went through this exact struggle, I can't recommend enough that you set up quarterly estimated tax payments if you haven't already - it makes SEP IRA planning so much easier! When you're paying estimated taxes quarterly, you get a much clearer picture of your actual net self-employment earnings throughout the year. I use a simple tracking spreadsheet where I log my income and expenses monthly, then calculate my running SEP IRA contribution limit. This helps me make smaller contributions throughout the year instead of scrambling at tax time. The key insight that helped me was realizing that your SEP IRA contribution is essentially an additional business deduction that reduces your taxable income. One thing to watch out for with variable income - don't max out your contributions early in the year based on a good quarter, because if your income drops later you might exceed the limits. I learned this the hard way and had to deal with excess contribution penalties. Better to contribute conservatively throughout the year and make a final catch-up contribution after you know your actual annual numbers.

I've been dealing with this same issue for years as a self-employed consultant! One approach that's worked really well for me is using TurboTax's self-employed version - not just for filing taxes, but their mid-year planning tools are fantastic for SEP IRA calculations. The key thing I learned is to be conservative with your projections when income varies month to month. I typically calculate my SEP contribution limit based on 80-90% of what I think my annual income will be, then make a final "true-up" contribution in the following tax year once I know my exact numbers. Also, don't forget that if you have any employees (even part-time), you'll need to contribute the same percentage for them as you do for yourself - this caught me off guard my first year. The SEP IRA rules require equal treatment for all eligible employees. For tracking throughout the year, I just keep a simple spreadsheet with monthly income/expenses and recalculate my projected contribution limit each quarter. It's not perfect but keeps me in the ballpark without overthinking it.

2 Has anyone used H&R Block for S-corp returns? They quoted me $350 which is cheaper than both options the original poster mentioned.

I can help clarify the extension process for S-corps since someone asked about it. You can file Form 7004 to get an automatic 6-month extension, which pushes the deadline from March 15th to September 15th. However, this is only an extension to FILE, not to pay any taxes owed. The key thing with S-corps is that even if you had losses like the original poster, you still need to file the return by March 15th (or September 15th with extension) because the K-1s that flow to your personal return are needed for your April 15th personal filing deadline. Also regarding H&R Block - I've seen mixed results with their S-corp preparation. Their seasonal preparers often lack the specialized S-corp knowledge that dedicated business tax professionals have. For a simple first-year return with losses, they might be fine, but make sure whoever prepares it understands S-corp basis rules and proper documentation requirements for future years.

dont forget that for 2025 taxes the SALT deduction is still limited to $10k which means a lot of ppl with big mortgages dont even get to use their full mortgage interest deduction anyway! I've got like $24k in property taxes and state income tax but can only deduct $10k of it which sucks.

As someone who's dealt with multiple rental properties for years, I want to emphasize something that might get overlooked in all this discussion about the $750k limit and reporting requirements. Make sure you're also considering the timing of when you acquired each property and what the debt limits were at that time. If you took out your primary residence mortgage before December 15, 2017, you might actually be grandfathered under the old $1 million limit rather than the current $750k limit. This could significantly change your calculations, especially since your primary residence is around $820k. The grandfathering rules are complex but could save you thousands if you qualify. Also, since you mentioned this is your first year with the inherited rental property, don't forget that you may have gotten a stepped-up basis on that property when you inherited it. This could affect your depreciation calculations on Schedule E, which is separate from but related to your mortgage interest treatment. I'd strongly recommend consulting with a tax professional who specializes in real estate, especially for your first year handling multiple properties. The potential tax savings from proper planning usually far exceed the cost of professional advice.

I don't think anyone mentioned this, but if you have professional tax software like UltraTax or Lacerte, they can batch generate all these forms for you. I had to do this for a client with 12 missing quarters and it saved a ton of time.

I went through this exact situation with my S-Corp about 6 months ago! Had to file 20+ zero 941s after getting a similar notice. Here's what worked for me: 1. I did file all the back quarters on paper forms - yes, it's tedious but necessary 2. I checked box 18 on each form as others mentioned 3. Most importantly, I included a cover letter explaining that we only do annual payroll in December and that all other quarters have zero wages The key thing that helped me avoid penalties was being proactive. I called the IRS business line (using that Claimyr service someone mentioned - totally worth it to skip the hold time) and spoke to an agent who noted in my file that I was actively resolving the issue. Pro tip: You can download the PDF forms from the IRS website and fill them out electronically before printing. Makes it much faster than handwriting 27 forms. Also, consider sending them certified mail so you have proof of delivery. The whole process took me about 3 hours spread over a weekend, but it completely resolved the issue and I haven't gotten any more notices. Now I just file a zero 941 each quarter after December payroll.

This is a really thoughtful question and I'm glad you're being proactive about it! Based on what you've described, this shouldn't be considered a gift for tax purposes. The key factor the IRS looks at is actual ownership and control of the money, not just whose names are on the account. Since your brother deposited his own settlement money and it's clearly understood between you both that it remains his money (he's just using the joint account as a budgeting tool), no gift has occurred. You're essentially acting as a trustee or helping him with money management, not receiving ownership of the funds. That said, I'd definitely recommend documenting this arrangement in writing - just a simple signed statement from both of you explaining that the money belongs to your brother despite being deposited in the joint account for financial discipline purposes. Keep this with your tax records along with any documentation of the original settlement. If the IRS ever questions it down the line, you'll have clear evidence of your intent. Also worth noting that any interest earned on that money while it's in the account should probably be reported on your brother's taxes since it's technically his money earning the interest.

I appreciate all the detailed responses here! As someone who's dealt with similar joint account situations, I want to emphasize one more important point: make sure you both understand the implications if your brother ever decides to withdraw the money. Since it's a joint account, technically either of you could withdraw the funds at any time, which is something the IRS might consider if they ever audit this situation. The fact that you're not treating it as "your" money and have an understanding that it belongs to your brother is crucial, but having that written agreement that others mentioned becomes even more important. Also, consider what happens if your brother uses some of the money but leaves the rest in the account for an extended period. The longer it stays there, the more it might look like a gift arrangement to an outside observer. Keeping clear records of any withdrawals he makes (and ensuring they're for his purposes) will help maintain the "this is still his money" narrative. One practical suggestion: if your brother is serious about using this as a budgeting tool, maybe consider setting up automatic transfers to a separate savings account in his name only, rather than keeping such a large sum in a joint checking account indefinitely. This could accomplish his goal of controlled spending while eliminating any potential tax complications down the road.