Has anyone used TurboTax Self-Employed for estimated taxes? Their website says it can help calculate quarterly payments but I'm not sure if it's worth paying for the full year just to figure out my AGI for estimated taxes.

Great thread! As someone who made the same transition from W-2 to freelance last year, I can share what worked for me. The key thing I learned is that AGI calculation for estimated taxes is actually pretty straightforward once you break it down: Your AGI = Total Income - Business Expenses - Self-Employment Tax Deduction - Other Above-the-Line Deductions For variable income, I use what I call the "true-up method" each quarter: 1. Calculate my actual year-to-date AGI based on real numbers 2. Project what my full-year AGI will be based on current trends 3. Calculate the tax on that projection 4. Subtract what I've already paid in estimates 5. Pay 25% of the remaining balance (since there are 4 quarters) This keeps me from overpaying early in the year when income is low or underpaying when I have a good month. The IRS doesn't care if your payments are uneven as long as you hit the safe harbor amounts by year-end. Also, don't forget that as a freelancer, you can deduct things like your home office, business phone, professional development, and even some meals if they're business-related. These all reduce your AGI and lower your estimated tax burden.

This is such a helpful thread! I'm dealing with a similar situation where we have a client who changed their plan year mid-stream, resulting in both a short plan year (5 months) and a full plan year that need to be reported on the same Form 720. One thing I wanted to add that hasn't been mentioned yet - make sure you're also keeping detailed records of which calculation method you used for each period and why. We had an audit a few years back where the IRS wanted to see our justification for choosing the snapshot method versus actual count method, especially for the shorter period. Also, if you're using different methods for each period (which is allowed), document that clearly. For example, we used actual count for our short plan year because we had complete monthly data, but snapshot for the full year due to some data gaps. The IRS was fine with this approach as long as we could show our reasoning. The documentation suggestion from ApolloJackson about attaching an explanation sheet is spot on - it saved us a lot of back-and-forth when questions came up later.

This thread has been incredibly helpful! I'm dealing with a similar scenario where our client has both a 6-month short plan year and a full 12-month plan year that need to be reported together. One additional consideration I wanted to mention - if you're working with a self-funded client like the original poster, make sure they understand the payment timing. Even though you're filing both periods on the same Form 720, the payment is still due by July 31st for both periods. I've seen clients get confused thinking they have separate due dates for each plan year period. Also, for anyone using the snapshot method for their calculations, remember that you need to pick consistent dates within each plan year period. So if you're taking snapshots on the 15th of each month for your full plan year, stick with the 15th for all months in that period, and then you can choose different snapshot dates for the short plan year if that works better with your data. The advice about detailed documentation is spot on - I always create a simple spreadsheet showing the calculation for each period separately, then attach it to the Form 720. It makes everything much clearer if questions arise later.

With a 7-figure tax bill, have you considered family office services? Several wealth management firms offer comprehensive tax strategy as part of their family office packages. They coordinate everything including working with your existing CPA. We made the switch two years ago and our tax rate dropped by 6% the first year. They implemented strategies around timing of income recognition, charitable remainder trusts, and opportunity zone investments that our CPA had never suggested.

Based on your situation, I'd strongly recommend going the tax strategist route rather than switching CPAs again. You're absolutely right that the constant CPA churn is counterproductive - it takes them forever to understand complex structures, and you lose all that institutional knowledge each time. A good tax strategist will work collaboratively with your current CPA. Think of it as division of labor: the strategist identifies opportunities and creates the roadmap, your CPA handles the compliance and execution. This way you keep the relationship that already understands your entity structure while adding the proactive planning piece that's missing. With your effective rate climbing from 20% to 32% and a 7-figure tax bill, even a modest improvement could easily justify the strategist's fees. Look for someone who specializes in equity investments and multi-entity structures specifically - they should be able to show you concrete examples of strategies they've implemented for similar clients. The key is finding someone who provides detailed implementation guidance with IRS code citations, not just vague suggestions. Your CPA will be much more receptive to executing strategies when they have clear legal backing and step-by-step instructions.

has anyone ever had their wfh stipend audited? i'm getting $200/mo but honestly my internet is only $65 and i don't really spend much on supplies. kinda worried im going to get in trouble someday but also my company doesn't ask for receipts?

This is such a timely question! I'm dealing with something similar and want to share what I've learned through research and talking to my HR department. The key thing to understand is that there are really two different approaches companies can take with WFH stipends, and they have very different tax implications: 1. **Taxable stipend/allowance**: The company just adds the money to your paycheck. This gets taxed as regular income, and since most of us are W-2 employees, we can't deduct the home office expenses to offset it (thanks to the TCJA changes through 2025). 2. **Accountable plan reimbursement**: You submit receipts/documentation for actual expenses, and the company reimburses you. This isn't considered taxable income. To figure out which one you have, look at your paystub. If you see the $250 listed in your gross wages, it's option 1. If it doesn't appear there at all, your company likely has an accountable plan set up. One thing I'd recommend is keeping detailed records of your actual home office expenses regardless of how your company handles it. Even if you can't deduct them now as a W-2 employee, it's good documentation to have, and tax laws could change in the future. Plus, if you ever transition to freelance/contract work, you'll want that history!

Has anyone figured out if this issue exists in TaxSlayer or H&R Block software too? I've been using FreeTaxUSA for personal returns but was planning to use TaxSlayer for my S-Corp this year.

This is a really helpful thread! I'm dealing with a similar SEHI deduction issue as an S-Corp owner. Just to clarify - when you manually entered the APTC repayment amount in the S Corp Health Insurance Premiums field, did you enter the full APTC repayment amount, or did you have to calculate some percentage of it? I'm trying to figure out if the entire APTC repayment becomes eligible for SEHI deduction, or if there's additional calculation needed based on the number of months covered or income levels. My APTC repayment was about $1,800 but I want to make sure I'm not claiming more SEHI deduction than I'm actually entitled to. Also, for anyone who's been through an audit - do you know if the IRS typically scrutinizes SEHI deductions heavily when they're manually entered like this instead of being automatically calculated by the software?