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Thanks everyone for the detailed responses! This is incredibly helpful. I've been stressing about this since the sale went through in January. Based on what you've all shared, it sounds like I have two main options: 1. Split the payments equally across four quarters (~$65k each for federal, plus the Washington state portion) 2. Use the annualized income installment method since all my gains happened in Q1 I'm leaning toward the annualized method since it seems more accurate for my situation, but I'm definitely going to keep detailed documentation as @StarGazer101 mentioned. One follow-up question - for the Washington state capital gains tax that @Yara mentioned ($73,500 on the amount over $250k), do they follow the same quarterly schedule as federal? And can I use the annualized method for state taxes too? Also going to check out both taxr.ai and potentially use Claimyr to get official IRS confirmation. With amounts this large, I'd rather be 100% certain I'm doing everything correctly. Better safe than sorry!
Welcome to the community! For Washington state's capital gains tax, yes they do follow the same quarterly payment schedule as federal (April 15, June 15, September 15, and January 15). You can absolutely use the annualized income installment method for Washington state taxes too, which makes sense given your situation with all gains in Q1. Since you're new to dealing with large capital gains, I'd definitely recommend getting that IRS confirmation through Claimyr - especially with both federal and state obligations totaling over $330k. Having official guidance will give you confidence you're handling everything properly. The annualized method sounds like the right approach for your situation, but documentation will be key if either jurisdiction questions your calculations later.
Welcome to the community! Just wanted to add another perspective as someone who went through a similar large capital gains situation. One thing that really helped me was setting up a separate savings account specifically for the tax payments and transferring the estimated amounts immediately after the sale. With $1.3M in gains, you're looking at roughly $260k federal + $73.5k Washington state = ~$333k total. Having that money physically separated from my regular accounts prevented any temptation to spend it and gave me peace of mind. Also, since you mentioned this is your only income for 2025 during your sabbatical, make sure you're not missing any deductions you might be eligible for. Things like investment advisory fees, safe deposit box fees, or other investment-related expenses might help reduce your taxable gains slightly. The annualized method definitely sounds right for your Q1 sale situation. Just remember that even though it's more complex, it can save you from having large amounts tied up in overpayments to the government throughout the year. Good luck with everything!
Great advice about setting up a separate account! I'm actually just getting started with investing and this thread has been incredibly educational. I had no idea there were quarterly estimated payments required for capital gains - I thought you just paid everything when you filed your tax return. Quick newbie question: when you mention "investment advisory fees" as potential deductions, are those still deductible? I thought I read somewhere that miscellaneous itemized deductions were eliminated in recent tax changes. Or is this something different? Also, do you know if there's a minimum threshold for needing to make quarterly payments? Like if someone had smaller gains (say $50k), would they still need to do this whole quarterly payment thing?
I think most people misunderstand REPS. The key issue is "material participation" in rental activities. Being a realtor counts for the 750 hours but NOT for material participation in your rentals. The exception is if you make a grouping election as others mentioned. Your CPA should know this but many don't understand real estate tax rules well. Just FYI - I got audited on this exact issue in 2023. The IRS was looking specifically at REPS claims. Make sure you have a detailed time log showing hours for EACH activity. After-the-fact estimates won't cut it in an audit.
Which form do you use to make the grouping election? Is it something specific or just a statement attached to your return?
Based on my experience dealing with REPS qualifications, your tax preparer may be being overly conservative. As a full-time realtor, you likely already meet the first two REPS requirements (750+ hours and 50%+ of working time in real estate). The critical piece is making the grouping election to treat all your rental activities as one activity. This election is made by attaching a statement to your tax return - there's no specific IRS form for it. The statement should clearly indicate you're electing to group all rental real estate activities under IRC Section 469(c)(7)(A). With this election, you can combine your time spent on the 3 self-managed properties with time spent overseeing the other 15 properties (reviewing reports, making decisions, communicating with property managers, etc.) to meet the material participation test. I'd recommend getting a second opinion from a CPA who specializes in real estate taxation. Many general tax preparers aren't familiar with the nuances of REPS, especially the grouping election strategy. The potential tax savings make it worth exploring further. Also, start keeping detailed time logs NOW for 2025 - document every hour spent on rental activities, no matter how small. This contemporaneous documentation is crucial if you're ever audited.
This is really helpful information! I'm in a similar situation as the original poster - working as a realtor but also have some rental properties. One thing I'm still unclear on though: when you make the grouping election, does that election apply permanently going forward, or can you make it year by year? Also, if you group all your rental activities together, are there any downsides to doing this election that people should be aware of before making this decision?
I'm going through the exact same nightmare! Filed 1/22 and still showing absolutely nothing on transcripts, WMR, or SBTPG. After reading through all these helpful suggestions, I'm planning to try multiple approaches tomorrow morning. First, I'll call the Taxpayer Advocate Service at 877-777-4778 around 7:45 AM based on Miguel's success story - the fact that they actually assigned a case advocate who followed up is exactly what I need right now. If that doesn't work out, I'll try the 866-682-7451 ext 569 number that several people have had success with. The Spanish language line idea is also brilliant - I speak both languages so that could be another option if the English lines are jammed. At this point, after almost 7 weeks with zero updates, I think we definitely qualify for TAS assistance since we've clearly exhausted normal channels. Thanks everyone for sharing your experiences - it's reassuring to know we're not alone in this frustrating situation!
Your multi-pronged approach sounds really smart! I'm in a similar boat (filed 1/28, zero movement anywhere) and I think you're absolutely right that after 7 weeks we definitely qualify for TAS assistance. The timeline Miguel shared gives me hope too - having an actual case advocate who follows up is exactly what we need instead of just getting lost in the phone system maze. I'm definitely going to try that early morning TAS call strategy as well. It's so frustrating that we have to become experts in navigating IRS phone systems just to get basic information about our own returns, but at least we're all sharing strategies that actually work. Please update us on how your calls go tomorrow - I'll be trying the same approach and would love to know if you have success!
I'm dealing with the exact same timeline - filed 1/24 and it's been complete radio silence! Your strategy of trying multiple approaches sounds perfect, and I'm definitely going to follow the same game plan. The early morning TAS call at 7:45 AM seems like our best bet based on Miguel's success story. I'm also bilingual so the Spanish line option could be a great backup plan. After 6+ weeks with absolutely nothing showing up anywhere, we've more than earned the right to TAS assistance. This whole situation is beyond frustrating - we shouldn't have to become IRS phone system experts just to find out what's happening with our own money! I'll be trying these same numbers tomorrow morning too, so hopefully between all of us someone will get through and can share what they learn. Fingers crossed we all get some answers soon!
I'm in the exact same situation and it's incredibly frustrating! Filed 1/29 and haven't seen any movement on transcripts, WMR, or SBTPG either. After reading through everyone's experiences here, I'm convinced that calling the Taxpayer Advocate Service at 877-777-4778 early in the morning is our best shot. Miguel's success story really gives me hope - having an actual case advocate assigned who follows up sounds like exactly what we need after weeks of getting nowhere with the regular IRS lines. I'm also going to try the 866-682-7451 ext 569 number as a backup plan. It's ridiculous that we have to become phone system ninjas just to get basic information about our own returns, but I'm grateful everyone is sharing what actually works. Will definitely update if I manage to get through - we're all in this together!
Just to add to all this great advice - I made the mistake of assuming Cash App would handle everything my first year too. Got a nasty letter from the IRS about missing 1099s! One thing that really helped me was setting up a separate business account on Cash App just for contractor payments. This makes it SO much easier to track business vs personal transactions when tax time comes around. You can still use your personal account for regular stuff, but having that separation saved me hours of sorting through transactions. Also, pro tip: start a simple spreadsheet right now with columns for date, contractor name, amount, and description of work. Update it every time you make a payment. Takes 30 seconds but will make preparing those 1099s in January a breeze instead of trying to reconstruct everything from your transaction history. Trust me on this one!
This is exactly what I needed to hear! Setting up a separate business account is such a smart idea - I've been mixing everything in my personal Cash App and it's already getting confusing trying to figure out which payments were for business. The spreadsheet tip is gold too. I'm definitely going to start that today before I forget any more details about the work that was done. Better late than never, right? Do you think it's worth going back through my transaction history to fill in the earlier payments from this year, or should I just start fresh from now and try to piece together the old stuff later? Also, that IRS letter situation sounds terrifying! How did you end up resolving that? I really don't want to deal with that kind of stress next year.
Great question! I went through this exact same confusion last year. The bottom line is YES, you absolutely need to issue a 1099-NEC to your subcontractor regardless of using Cash App. The payment method doesn't change your obligation as the business owner. Here's what I learned: Cash App may or may not issue a 1099-K to your contractor depending on whether they meet the threshold requirements, but that's completely separate from your responsibility. The 1099-K reports payment transactions, while your 1099-NEC reports the business relationship and compensation for services. At $27k, you're way over the $600 threshold that requires a 1099-NEC, so there's no question you need to file one. Don't worry about "double taxation" - your contractor will only report the income once on their tax return, they'll just have multiple forms documenting the same payments. My advice: get that W-9 from your contractor ASAP if you don't have it already, and start organizing your payment records now. January will be here before you know it and you'll need all the documentation ready to file by January 31st. Better to be prepared now than scrambling later!
This is really reassuring to hear from someone who's been through it! I was getting so worried about messing something up since this is all new to me. Quick follow-up question though - when you say "start organizing your payment records now," what exactly should I be documenting besides just the payment amounts? I've got all the Cash App transaction history showing the dates and amounts, but I'm wondering if I need more detailed records about what specific work was done for each payment. Some of my payments were for ongoing work over several weeks, so it's not always a 1:1 match between payment and specific project. Is that going to be a problem, or is the total amount for the year what really matters for the 1099?
Ethan Anderson
I'm dealing with this exact situation too! Filed on 2/18, accepted immediately, and Tax Topic 152 vanished about a week ago. Now it's just the dreaded "still processing" message with no transcript available. What's been really helpful for managing the anxiety is checking the IRS Processing Statistics page - they're currently running about 2-3 weeks behind their normal timelines due to staffing issues and increased verification procedures this year. Seeing the actual data helped me realize this isn't personal to my return. For your medical procedure payment, definitely reach out to the provider's billing department. Most have hardship or payment plan options, and many are familiar with tax refund delays. I had to do something similar last year and they were surprisingly accommodating. One tip that's saved my sanity: I switched to checking WMR only on Fridays. The daily checking was driving me crazy with no changes. Most updates seem to happen over weekends anyway based on what I've read in various forums. Hang in there - from everything I'm seeing, mid-February filers are all hitting the same processing bottleneck right now. It's frustrating but appears to be completely normal for this tax season! πͺ
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Elijah O'Reilly
β’The Friday-only checking strategy is genius! I've been refreshing WMR like every few hours and it's absolutely torturing me. Definitely going to try limiting myself to once a week - the constant disappointment of seeing the same "still processing" message is wearing me down. That IRS Processing Statistics page sounds really useful too. Do you have a direct link to it? I've been trying to find actual data about current processing delays but the IRS website is such a maze. Having real numbers would definitely help put this delay in perspective instead of just wondering if something's wrong with my specific return. Thanks for sharing the practical tips about both the mental health aspect and the billing department approach. It's so reassuring to know that literally everyone who filed mid-February is going through this same frustrating limbo right now! π
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Effie Alexander
I'm in the exact same situation and it's incredibly frustrating! Filed on 2/16, accepted immediately, Tax Topic 152 disappeared last week, and now just "still processing" with no transcript available. I was also counting on this refund for an upcoming medical expense (surgery scheduled for early April). What's helped me cope with the anxiety: β’ I called my surgeon's billing office and explained the situation - they were totally understanding and let me set up a payment plan where I pay 50% upfront and the remainder when my refund comes in β’ Stopped checking WMR daily (was driving me insane) and now only check on Mondays β’ Started following some tax professional accounts on social media who post updates about IRS processing delays - helps me feel less alone in this From everything I'm reading here and elsewhere, it seems like there's a massive bottleneck affecting mid-February filers specifically. The lack of communication from the IRS is maddening, but at least we're all in this together! One question for everyone - has anyone who filed around the same timeframe (mid-February) actually gotten their refund yet? I'm trying to get a sense of whether people are starting to see movement or if we're all still stuck in the same processing queue. Hang in there! π
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Giovanni Colombo
β’I'm so glad you asked about whether anyone has gotten their refund yet! I filed on 2/15 and just got my refund deposited yesterday morning - so there is hope! My timeline was almost identical to yours: Tax Topic 152 disappeared after about 3 weeks, then "still processing" for another 10 days, and then suddenly my transcript updated on Friday night and the money was in my account Monday morning. Your approach with the surgeon's billing office sounds perfect - that's exactly what I did with my car repair (which is what I needed my refund for). Most medical providers are super understanding about tax refund delays since it's so common this time of year. It's really reassuring to see so many people with the same exact timeline and experience. Makes it clear this is just a processing bottleneck and not individual return issues. Based on my experience, I'd guess most of us mid-February filers will start seeing movement in the next week or two. The waiting is awful but it does eventually resolve! πͺ
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