Has anyone used TurboTax to figure this out? I'm in a similar situation and the software is confusing me.

Just wanted to add some clarity based on my experience as a tax preparer - the key issue here is understanding what "keeping up a home" means for HOH purposes. The IRS defines this as paying more than half the cost of rent, mortgage interest, real estate taxes, insurance on the home, repairs, utilities, and food eaten in the home. Since you're paying 65% of these household maintenance costs, you definitely qualify for HOH with your son as your dependent. However, your girlfriend would need to show she pays more than half of these same household costs to qualify for HOH with your daughter. This is where it gets tricky - you can't both be paying more than half of the same expenses. The child-specific expenses your girlfriend pays (daycare, clothing, medical) are important for determining who can claim the child as a dependent, but they don't count toward the "keeping up a home" test for HOH status. My recommendation: You claim HOH, and your girlfriend should probably file as Single (assuming she can't demonstrate paying more than half of household maintenance costs). You'll both still claim your respective children as dependents and get those tax benefits. Consider consulting a tax professional to review your specific numbers - this is one of those situations where the details really matter for compliance.

Did you receive any CP01 notices? Those indicate identity verification issues. Have you checked your transcript for TC 570 codes? What about your account transcript - sometimes that updates before your return transcript.

I've seen this pattern before - when multiple tax years are being held simultaneously along with missing CTC payments, it often indicates a systemic account flag rather than just a processing delay. The fact that your return isn't even showing in the system after this long suggests it may be stuck in the Taxpayer Protection Program queue. Have you tried requesting your Account Transcript (not just Return Transcript) through IRS.gov? Sometimes the account transcript will show transaction codes even when the return transcript is blank. Also, if you haven't received any correspondence from the IRS at all, I'd recommend updating your address on file - sometimes verification letters get sent to old addresses and the lack of response keeps the account frozen.

As someone who just went through estate administration myself, I can't stress enough how important it is to get this fiscal year decision right from the start. You're absolutely on the right track thinking strategically about this. One thing I learned the hard way - document everything meticulously when you make your fiscal year election. Keep records of when each income item was received and when expenses were incurred. The IRS can be very particular about the timing, especially if they ever audit the estate return. Also, since you mentioned expecting more income after October, consider whether any of that income might be recurring (like rental income, dividend payments, etc.). If so, you'll want to factor that into your long-term tax planning strategy beyond just this first fiscal year. Have you considered consulting with a CPA who specializes in estate taxation? Given the complexity of balancing the fiscal year choice with distribution timing and the relatively compressed estate tax brackets, the cost of professional advice often pays for itself in tax savings. Plus, they can help ensure you're not missing any deductions that estates are entitled to claim.

Having dealt with estate administration recently, I'd add one more strategic consideration to what's already been shared here. Since you're expecting more income after October, think about whether that timing creates an opportunity for multi-year tax planning. If you set your fiscal year to end July 31st (which seems optimal given your May expense and July income), you could potentially time future distributions in subsequent years to smooth out the tax impact. For example, if you know significant income is coming in November-December, you might want to make distributions to beneficiaries early in that next fiscal year to offset the higher income. Also, don't overlook the estate's standard deduction ($300 for 2024/2025) and personal exemption ($100) - they're small but every bit helps with these compressed tax brackets. One practical tip: if you do decide to use the 65-day rule for distributions, mark those dates clearly on your calendar now. It's easy to lose track of deadlines when you're juggling all the other aspects of estate administration. The October 4th deadline (65 days after July 31st) would be critical for your tax planning to work properly. The documentation advice from others here is spot-on - the IRS loves clear paper trails, especially for timing elections that affect multiple tax years.

Based on your complex situation with two trusts plus personal returns, I'd actually recommend considering a hybrid approach. I've been in a similar position as trustee for multiple family trusts, and what worked best for me was using professional software for the trust returns but then importing the K-1 data into a consumer program for my personal return. For the trust returns specifically, I found that the AI-powered solutions like taxr.ai (mentioned above) or professional software like ProSeries give you the most accurate results for the complex trust accounting rules. The consumer programs like TurboTax just aren't built to handle the nuances of trust income allocation, especially when you're dealing with investment income versus IRA distributions with different tax treatments. One thing to keep in mind - since you're dealing with inherited IRA distributions based on life expectancy tables, make sure whatever software you choose is current on the SECURE Act changes. Some of the older professional packages haven't updated their life expectancy calculation modules properly. Also, given the complexity, I'd strongly recommend having at least a consultation with a trust tax specialist for your first year to make sure you're setting up the calculations correctly. You can then use that as a template for future years with whatever software you choose.

As someone who's been through this exact scenario, I can tell you that handling multiple trust returns plus personal taxes is definitely doable but requires the right approach. I manage two family trusts (one with investments, one with retirement accounts) plus my own return. From my experience, the key is making sure your software can properly handle the trust accounting rules - specifically the distinction between distributable net income (DNI) and how different types of income flow through to the K-1s. This is where a lot of consumer software falls short. I'd echo what others have said about considering the professional-grade options, but also want to mention that you'll need to be very careful about the timing of distributions if you have any control over that. The tax implications can vary significantly depending on whether distributions happen before or after year-end, especially with the investment trust. One practical tip: whatever software you choose, make sure it can handle the Schedule K-1 reconciliation properly. I learned this the hard way when my first year's returns didn't properly tie out between the trust returns and my personal return, which triggered an IRS notice. Also, since you're on Mac, I've found that running Windows software through VMware Fusion works better than Parallels for tax software - seems to handle the printing and PDF generation more reliably, which you'll need for filing and record keeping.

This thread has been incredibly helpful! As someone who works in tax preparation software support, I see this confusion about DCNs all the time. You're definitely not alone in not knowing about this number! The DCN is essentially your tax return's unique identifier in the IRS system - think of it like a tracking number for a package, but for your entire tax return. While you don't need it for everyday things like checking refund status, it becomes invaluable when you need to speak with an IRS representative about specific issues. Since you mentioned using TaxAct, here's the easiest way to find your 2023 DCN: 1. Log into your TaxAct account 2. Navigate to "My Returns" or "Tax Home" 3. Select your 2023 tax year 4. Look for "Filing Details" or "Submission Summary" 5. The DCN should be listed there, usually labeled as "Declaration Control Number" or just "Control Number" Pro tip: Once you find it, save it in a secure note or document along with your filing date and confirmation number. I always recommend clients treat their DCN like they would any other important financial reference number - you hope you never need it, but when you do, you'll be so glad to have it readily available! The good news is that if you ever can't locate it, any future IRS correspondence will include your DCN, so don't stress too much about tracking down old ones unless you're actively dealing with an issue.

This has been such an informative thread! I'm relatively new to filing my own taxes (just started a few years ago after being claimed as a dependent) and honestly had no idea DCNs even existed until reading through everyone's experiences here. What really helped me understand this was @Chloe Martin's example about needing it for the stimulus payment issue - that makes it so much more concrete than just "it's a tracking number." The fact that the IRS rep immediately found her return once she provided the DCN really shows how important it is from their perspective. I use H&R Block online and just went hunting for my DCN after reading all these responses. Found it in my account under "View Your Return" in a section called "E-file Information." It was right there next to the acceptance date, but I had completely overlooked it before! I'm definitely going to start a tax organization system like @Ravi Patel and @Omar Farouk suggested. The idea of keeping all the important numbers (DCN, confirmation, prior year AGI) in one easily accessible place seems like such a simple way to avoid future headaches. Thanks @Javier Morales for asking this question - clearly a lot of us needed this education! This community continues to be such a great resource for practical tax knowledge that you don't learn anywhere else. 💪