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Don't forget to check if your state handles inherited property the same way the IRS does! NY generally follows federal rules, but some states have their own twists on capital gains for inherited property. Just something to double-check.
Mei Wong
ā¢Good point. I inherited property in California and the rules were slightly different than federal. Had to file special paperwork with the county assessor too. Check with your state tax department to be sure.
Zara Khan
This is a great question about Section 121 and inherited property! I went through something similar when I inherited my grandmother's house through intestate succession in Pennsylvania. One thing I learned that might be helpful - you should also consider getting a professional appraisal for the property's value at the date of death if you don't already have one. This establishes your stepped-up basis officially and can be crucial if the IRS ever questions your capital gains calculation. In my case, I had lived in the inherited house for 3 years before selling, so I easily qualified for Section 121. But even if I hadn't, the stepped-up basis meant my actual capital gain was much smaller than it would have been if I had purchased the property myself years ago. Also, make sure to keep detailed records of when you moved in and made it your primary residence. The IRS can be pretty strict about proving the 2-year residency requirement, so having utility bills, voter registration changes, and other documentation showing it was your principal residence will be important if you're ever audited.
This is really helpful advice about getting a professional appraisal! I hadn't thought about that but it makes total sense to have official documentation of the stepped-up basis. Do you know if there's a time limit for getting the appraisal done, or can I get one retroactively? I inherited the property about 2 years ago and didn't think to get an appraisal at the time. Also, did you use a specific type of appraiser or just any licensed real estate appraiser?
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Alicia Stern
This is such a complex situation, and I really appreciate everyone sharing their experiences here! As someone who's been dealing with similar back tax issues, I wanted to add a few thoughts. First, regarding the statute of limitations - it's worth noting that while you generally can't get a refund after 3 years, the IRS can still apply overpayments as credits to other tax years even beyond that timeframe in certain circumstances. The key is how you handle the filing process. One thing I learned the hard way is that the ORDER you file multiple years matters tremendously. If you file 2017 first and request the overpayment be applied to 2018, then file 2018 showing that credit, it's processed differently than if you file them simultaneously or in reverse order. Also, don't forget about estimated tax payments you may have made for 2019 that could be applied back to 2018 if needed. The IRS has more flexibility with moving payments between adjacent tax years than most people realize. I'd strongly recommend getting everything professionally reviewed before filing - the potential savings from doing this right the first time far outweigh the cost of professional help. Missing these nuances could cost you thousands in lost credits or unnecessary penalties.
Zainab Yusuf
ā¢This is incredibly helpful information! I had no idea that the filing order could make such a big difference. When you mention filing them simultaneously vs in reverse order - could you elaborate on what the best approach would be for someone in the OP's situation with a 2017 overpayment and 2018 underpayment? Also, you mentioned estimated tax payments for 2019 potentially being applied back to 2018 - how does that work exactly? I thought estimated payments could only be applied to the year they were intended for. Is there a specific form or process to request that kind of reallocation? I'm dealing with a similar mess (2016-2018 unfiled) and trying to figure out the optimal strategy before I make any costly mistakes. Your point about professional review is well taken - do you have any recommendations for finding someone who specializes in multi-year filing situations like this?
CosmicCadet
ā¢Great question about filing strategy! For the OP's situation (2017 overpayment, 2018 underpayment), the optimal approach would typically be to file both returns simultaneously in separate envelopes but mailed on the same day. On the 2017 return, you'd check the box to apply the overpayment to the following year rather than requesting a refund. This creates a clean paper trail showing your intent. Regarding estimated payments - yes, you can request reallocation! If you made estimated payments for 2019 but later determine you owed more for 2018, you can file Form 843 (Claim for Refund and Request for Abatement) to request those payments be moved back. The IRS has some flexibility here, especially when dealing with unfiled returns being caught up. For finding the right professional, look for an Enrolled Agent (EA) who specifically advertises experience with "back tax resolution" or "unfiled returns." They're often more cost-effective than CPAs for this type of work and have specialized training in IRS procedures. Many offer free consultations where they can review your specific situation and give you a filing strategy upfront. The key is finding someone who won't just prepare the returns but will analyze the optimal approach for your multi-year situation first.
Malik Davis
I've been following this thread as someone who went through a very similar situation with unfiled returns from 2016-2018. One thing I want to emphasize is the importance of acting quickly once you decide to file these old returns. The longer you wait, the more interest and penalties accumulate, and you risk losing additional credits. I procrastinated for an extra year after discovering my situation, and it cost me about $800 in additional interest that I could have avoided. Also, something that helped me was creating a simple spreadsheet tracking all my payments, estimated taxes, and what I owed for each year before I started filing. This gave me a clear picture of exactly how much I could recover and helped me set realistic expectations. When I finally filed, I was able to recover about 60% of what I thought I'd lost to the statute of limitations by following a strategic filing order and including the right forms. The key was understanding that while I couldn't get cash refunds for the older overpayments, I could still use them to offset other tax debts. Don't let the complexity paralyze you - even an imperfect filing is better than continuing to let these returns sit unfiled. The IRS is generally more willing to work with taxpayers who are making an effort to get compliant.
This is such valuable advice about acting quickly! I'm actually in this exact situation right now - discovered I have unfiled returns from 2017-2019 about six months ago and I've been paralyzed by all the conflicting information I've found online. Your point about creating a spreadsheet is brilliant - I keep getting overwhelmed trying to figure out what I owe vs what I paid in my head. Did you include estimated quarterly payments in your tracking as well? I made payments for some quarters but not others, and I'm not even sure which years they were applied to. The 60% recovery rate you mentioned gives me hope. I was starting to think I'd lost everything to the statute of limitations. When you say "strategic filing order," do you mean you filed the earliest year first, or did you file them in reverse chronological order? I keep seeing conflicting advice on this. Also, did you handle the filings yourself or work with a professional? I'm trying to decide if the cost of professional help is worth it given that I'm already facing penalties and interest charges.
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Olivia Clark
Has anyone dealt with this situation where the escrow company issued the 1099-S incorrectly? My brother and I sold our parents' house but the escrow company put the entire amount under my SSN even though we split it 50/50. Will this cause problems with the IRS?
Yes! This happened to me and my sister. The 1099-S had the full amount under my SSN. I reported only my half on my tax return and included a brief explanation in the notes. My sister reported her half on her return. We never heard anything from the IRS about it. Just make sure you both keep good records showing the 50/50 split.
Brian Downey
I went through something very similar when my sister and I inherited and sold our dad's rental property. One thing I'd add is to make sure you have the proper estate documentation showing the stepped-up basis value. We had to get a formal appraisal done as of the date of death because the estate didn't have one initially. Also, since you mentioned using TurboTax - when you get to the Schedule D section, there's a specific checkbox for "inherited property" that ensures the software treats it correctly for the stepped-up basis calculation. Make sure you check that box, otherwise it might try to use your parents' original purchase price as the basis, which would result in a much higher taxable gain. One last tip - if the house had any improvements made between the date of death and the sale date, you can add those to your basis as well. We had to do some minor repairs before selling and those costs reduced our taxable gain.
This is really helpful advice about the TurboTax checkbox for inherited property - I almost missed that! Quick question about the improvements you mentioned: do minor repairs like fixing a leaky faucet or touching up paint count as improvements that can be added to basis, or does it have to be more substantial work like a new roof or HVAC system? We had to do some basic maintenance before listing but I wasn't sure if those small expenses could reduce our taxable gain.
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I still get confused about this. Last year I overpaid by like $2 because I rounded up everything to be safe. Better than underpaying I guess but still annoying.
Aaliyah Reed
ā¢I've found the easiest approach is just to use tax software even for calculating estimated payments. Most of them have a quarterly payment calculator that handles all the rounding rules automatically. I use FreeTaxUSA and it does this pretty well without making you pay for the full tax prep service.
NeonNebula
I've been dealing with this same rounding issue for years! What finally helped me was creating a simple spreadsheet template that automatically rounds each figure to the nearest dollar before doing any calculations. For your specific numbers: $37,499.60 rounds to $37,500, $19,000.15 rounds to $19,000, so you'd owe $18,500. For state: $25,000.30 rounds to $25,000, minus $23,000 paid = $2,000 owed. The key is being consistent - always round individual amounts first, then calculate. I learned this the hard way after getting a small underpayment penalty one year because I was inconsistent with my rounding methods across different quarters. Now I use the same approach every time and haven't had any issues.
That spreadsheet idea is brilliant! I've been manually calculating everything and making rounding errors. Do you mind sharing what formulas you use in your template? I'm decent with Excel but not sure how to set up the automatic rounding for tax calculations. Also, have you found any issues with how the spreadsheet handles the safe harbor rules for estimated payments, or do you calculate those separately?
Ravi Malhotra
Great question! I was in a similar situation a few years ago and learned some hard lessons. With your combined income of around $63,000, you'll definitely want to be proactive about withholding. One thing to keep in mind is that restaurant work often involves tips, which are taxable income that may not have proper withholding. If you're serving tables, make sure to track all your tip income carefully and consider that when calculating your total annual earnings. The "different tax bracket" comment from your manager is referring to how your marginal tax rate increases as your income goes up. While you won't pay the higher rate on all your income (that's a common misconception), the additional $15K will likely be taxed at 22% instead of the 12% rate that covers most of your main job income. My recommendation: Use the IRS withholding calculator online to get specific guidance for your situation, or consider having extra tax withheld from your main job's paycheck. I'd rather get a refund than owe money when saving for a house down payment! Also, keep good records of any work-related expenses from the restaurant job.
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Eloise Kendrick
ā¢This is really helpful advice! I'm just starting to think about taking on a second job myself and hadn't even considered the tip income aspect. Quick question - when you mention keeping records of work-related expenses from restaurant work, what kinds of things typically qualify? I know the tax laws changed a few years back for employee deductions. Are there still legitimate deductions for restaurant workers, or is it mainly just important for tracking purposes?
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DeShawn Washington
ā¢You're absolutely right to ask about this! Unfortunately, since the 2018 Tax Cuts and Jobs Act, most unreimbursed employee expenses (including things like uniforms, non-slip shoes, or tools) are no longer deductible for W-2 employees. The tracking is mainly important now for tip income reporting and making sure your employer is properly withholding on declared tips. However, if you end up doing any delivery work as part of the restaurant job and use your personal vehicle, that could potentially be deductible if you're treated as an independent contractor rather than an employee. The key is understanding your employment classification - W-2 employee vs 1099 contractor makes a big difference for deductions. For most traditional restaurant employee roles though, the focus should really be on proper withholding and tip reporting rather than trying to find deductions. The withholding planning @Ravi mentioned is definitely where you'll get the most benefit!
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Mei-Ling Chen
Having been through this exact scenario myself, I'd definitely echo the advice about adjusting your withholding proactively. One thing I wish someone had told me when I started my second job - consider setting aside a small emergency fund specifically for potential tax surprises, even if you do everything right with withholding. With restaurant work, there are a few additional considerations beyond just the base wages. If you're in a tipped position, your employer might only withhold taxes on your hourly wage (which could be as low as $2.13/hour in some states) but not on your tips. This can create a significant underwitholding situation if your tips are substantial. Also, make sure both employers know about your multiple job status when filling out your W-4. There's actually a checkbox on the 2020 and newer W-4 forms (Step 2c) specifically for this situation. Don't be afraid to be conservative with your withholding - when you're saving for a house down payment, the last thing you want is to have that money tied up in an unexpected tax bill. The good news is that $63k total income is still very manageable from a tax perspective, and with proper planning you shouldn't have any nasty surprises come filing time!
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Yara Sayegh
ā¢This is such solid advice, especially about the emergency fund for tax surprises! I never thought about how low the tipped minimum wage could affect withholding. Quick question - when you mention the W-4 checkbox for multiple jobs, do both employers need to know, or is it enough to just check it on one job's form? I want to make sure I'm handling this correctly from day one. Also, your point about being conservative with withholding really resonates. I'd much rather get a refund than scramble to pay a big tax bill when I'm trying to save for a house. Better safe than sorry!
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Hannah White
ā¢Great question about the W-4 checkbox! Technically, you should check the multiple jobs box on both employers' W-4 forms for the most accurate withholding calculations. The IRS designed the form so that when both employers know about your multiple job situation, their payroll systems can coordinate better to avoid under-withholding. However, in practice, many people find it easier to just handle the extra withholding through their primary job (like adjusting line 4c for additional withholding) rather than trying to coordinate between two different HR departments. The key is making sure the total amount of tax withheld across both jobs covers your liability. Your instinct about being conservative is spot-on! When I was house shopping, I actually increased my withholding even more than the calculators suggested because I knew I couldn't afford any surprises. It meant smaller paychecks during the year, but having that peace of mind (and getting a nice refund right around house-hunting season) was totally worth it. You're already thinking about this the right way!
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