I'm going through a similar situation right now and this thread has been incredibly helpful! My divorce won't be final until May, but I've been separated since September and have my two kids living with me full-time. I was planning to file Married Filing Separately, but after reading about the Head of Household option, I'm wondering if I qualify too. One question I haven't seen addressed - if I do qualify for Head of Household, do I need any special documentation to prove the separation timeline or that I paid more than half the household expenses? I want to make sure I have everything properly documented in case the IRS has questions later. The last thing I need during this stressful time is an audit because I didn't have the right paperwork to back up my filing status. Also, for those who mentioned the tax calculation tools - do they factor in state taxes too? I'm in California and wondering if the filing status choice affects state taxes differently than federal.

As someone who works in tax preparation, I want to emphasize something that hasn't been fully addressed - the timing of when you actually separated matters a lot for Head of Household eligibility. The IRS requires that you lived apart from your spouse for the LAST SIX MONTHS of the tax year, not just any six months during the year. So if you separated in August like one commenter mentioned, you'd meet this requirement since August through December is more than six months. But if someone separated in July, they'd need to count July through December to make sure it's at least six months. Also, regarding documentation - the IRS doesn't require you to file proof with your return, but you should definitely keep records. I recommend creating a simple timeline document showing: separation date, when kids started living with you primarily, major household expenses you paid each month, and any relevant court documents or separation agreements. One more tip: if you're unsure about your filing status, you can always file an amended return if you discover you qualified for a more beneficial status after filing. It's better to be conservative and potentially amend later than to file incorrectly and face penalties. The Head of Household status can save significant money compared to Married Filing Separately, so it's definitely worth exploring if you think you might qualify!

Another option is to just increase your withholding at your day job if you have one. I just filled out a new W-4 and had my employer take out an extra $100 per paycheck to cover my side gig income. Way easier than figuring out quarterlies.

I use the "profit first" method for my business and it's been a lifesaver. I automatically set aside 25-30% of every payment I receive into a separate tax savings account. Then I have the money ready for quarterly payments no matter how irregular my income is.

One thing none of these comments mentioned - the SALT cap is scheduled to expire after 2025! So if you're buying a home now, in just a couple years the cap might go away and you could potentially deduct your full SALT amount again. Of course, Congress could extend the cap or create a new limit, but it's worth keeping in mind for long-term planning.

Great discussion everyone! As someone who went through this exact analysis last year, I wanted to add a few practical tips for @cc288379ec13: 1. Don't forget about PMI - if you're putting less than 20% down, your mortgage insurance premiums are also deductible (subject to income limits). This can add another $1-3k to your itemized deductions. 2. Track your charitable contributions more carefully once you're itemizing. Even small donations to Goodwill, church offerings, etc. can add up to meaningful deductions. 3. Consider timing some deductions strategically. For example, if you're close to the itemizing threshold, you might want to bunch charitable contributions into alternating years to maximize the benefit. The $18k property tax you mentioned is indeed high, but if you're in a state like NY, NJ, or CA, that's unfortunately pretty normal for decent areas. Just make sure you factor in the tax benefits when comparing the total cost of homeownership vs. renting. One last thing - property taxes can increase over time, but your deduction will still be capped at $10k, so factor that into your long-term planning.

Does anyone know if the "reasonable period" for winding up trust affairs is affected by whether the trust is revocable vs. irrevocable? My mother's irrevocable trust was terminated in December but we just found out about some stock that wasn't properly transferred and is still generating dividends.

I went through something very similar with my grandmother's trust last year. The key thing to understand is that the "reasonable period" mentioned in 26 CFR § 1.641(b) is specifically designed for situations like yours where income trickles in after the formal termination date. Your trustee is correct - the trust is still considered to exist for tax purposes during this winding-up period. The $4,600 in dividends should be reported on an amended final Form 1041 for the trust, not on your individual returns. The trustee will then need to issue supplemental K-1s to you and your siblings showing your respective shares of this additional income, which you'll report on your personal returns. The fact that the bank statement arrived months later is actually pretty common - I've seen this happen with everything from dividend payments to final interest statements. As long as the trustee is actively working to wrap up all loose ends (which discovering and reporting this income demonstrates), you're well within the reasonable timeframe. One tip: make sure the amended return clearly indicates it's for post-termination income to avoid any IRS confusion about the filing.

I switched from TurboTax to FreeTaxUSA last year specifically because of K-1 issues. FreeTaxUSA handles K-1 entries much more intuitively and puts everything on the right schedules automatically. TurboTax is notorious for hiding the K-1 entry screens unless you know exactly where to look, and their support staff often give contradictory advice as you've discovered. With FreeTaxUSA, it's all clearly labeled and you can see exactly where your K-1 items are flowing on your return.

As someone who's dealt with this exact situation, I can confirm what others are saying - partnership K-1 income must go on Schedule E, Part II, never on Schedule C. The confusion happens because TurboTax Self-Employed is really designed for sole proprietors, not partnership members. Here's what worked for me: First, upgrade to TurboTax Premier if you're still on Self-Employed - it has much better K-1 support. Then go to Federal > Income & Expenses > Less Common Income > Partnership/S-Corp K-1. This will properly flow everything to Schedule E. The key is understanding that Schedule C is only for businesses you personally own and operate. Since you're a member of an LLC partnership, you're not operating the business directly - you're receiving your share of the partnership's income/loss through the K-1, which is why it goes on Schedule E. For your amended return, make sure to remove any partnership income that might have been incorrectly reported on Schedule C to avoid double-counting. The IRS is very particular about this distinction, so getting it right now will save you headaches later.