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There's actually another interesting historical reason for the stepped-up basis rule. Before computer records, tracking basis across generations would have been administratively impossible. Imagine trying to determine what your great-grandfather paid for a piece of land in 1910! The policy emerged partly from practical necessity - tax authorities simply couldn't verify original basis claims for inherited assets. Today we might have better record-keeping capabilities, but the policy remains entrenched.

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Zara Mirza

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Do other countries handle this differently? I'm curious if this is just a US thing or if most tax systems have something similar.

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Great question! Many countries actually do handle this quite differently. Canada, for example, treats death as a "deemed disposition" - essentially as if the deceased had sold all their assets at fair market value right before death, triggering capital gains tax at that point. The heirs then receive the assets with a basis equal to that fair market value. Australia, the UK, and Germany have various forms of inheritance or estate taxes but generally don't have the pure step-up in basis that the US offers. The US system is relatively unique in how completely it wipes out unrealized gains at death.

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NebulaNinja

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Has anyone seen the proposals to eliminate the stepped-up basis? I know it was part of Biden's initial tax plan but I'm not sure if it's still being considered. Would significantly impact a lot of estate planning strategies if that happened.

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Luca Russo

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Last I heard, they were considering limiting it rather than eliminating it entirely. Something like the first $1-2 million in gains would still get stepped-up, but anything above that would carry over the original basis. Hasn't passed but keeps coming up in tax reform discussions.

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The whole refund advance industry is basically legalized predatory lending imo. They target people who need money desperately and charge insane fees. I worked for one of the big tax prep chains for two seasons and quit because I felt like I was scamming people. Here's what they don't tell you: - The "no fee" advances are usually only for small amounts ($500-$1000) - Larger advances have fees that equal crazy high interest rates - Your credit score WILL be checked despite what they might imply - Many people get denied AFTER paying prep fees - If there's ANY issue with your return (even minor), you get denied The tax prep fees are also usually inflated to cover the "free" small advances. You're better off filing yourself with free software and waiting the 2-3 weeks for direct deposit.

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Thanks for the insider perspective! Quick question - since I already paid and they filed my return, is there any way to still get an advance elsewhere or am I stuck waiting for the normal refund now? My emergency isn't going to wait 3 weeks unfortunately.

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Unfortunately, once your return is filed, you can't get an advance from another company. The advance loans are tied to the preparation process, and you can only file once. Your best option now is to track your refund closely using the IRS "Where's My Refund" tool and consider other short-term options for your emergency. If you filed electronically with direct deposit, many refunds are coming through faster than the 21-day estimate this year - I've seen some clients get theirs in 10-14 days. Much better than payday loans or credit card advances, which have even worse terms than refund advances.

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Ryder Greene

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Has anyone actually gotten their regular refund faster this year? The IRS site says I'm still "processing" after almost 3 weeks and I've heard nothing.

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The IRS is running about on schedule this year for most simple returns, but there are definitely delays for returns with certain credits like EITC or Additional Child Tax Credit. Those are automatically held until mid-February by law. Returns with inconsistencies, verification flags, or identity theft markers also get delayed for manual review. If you're hitting the 21-day mark with no updates, it might be worth contacting the IRS directly to see if there's an issue they're not showing on the tracker.

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Miguel Ramos

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One thing nobody's mentioned yet - make sure you have good records of your original contributions. The whole "only pay taxes on the gains" thing depends on being able to prove you already paid taxes on the initial contributions. I learned this the hard way and had to pay taxes on the full conversion amount because I couldn't adequately document my non-deductible contributions from previous years.

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What kind of documentation should I keep? I have confirmation emails from my brokerage showing the contributions, and I have last year's tax returns. Is that enough?

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Miguel Ramos

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Confirmation emails are a good start, but you really want your account statements showing the contributions. Keep your Form 5498s that show IRA contributions for each year - these are usually sent out in May for the previous tax year. Your tax returns are crucial too, especially if you filed Form 8606 with them. If you didn't file 8606 forms for those non-deductible contributions, you should file amended returns to include them. Without the 8606 forms establishing your basis, it becomes much harder to prove which portions were already taxed.

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Has anyone here used TurboTax to handle an IRA conversion? I'm in a similar situation and wondering if it walks you through Form 8606 correctly or if I should use a different software.

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Zainab Omar

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I used TurboTax last year for my backdoor Roth and it worked fine. The interview questions specifically asked about non-deductible contributions and IRA conversions. Just make sure you answer the questions about having a basis in your IRAs correctly. The one tricky part was making sure I entered the 1099-R information exactly as it appeared on the form.

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How do individuals without a business entity file 1099-NEC and 1099-INT with the IRS? IRIS requires EIN but I'm just a landlord

This is my first year having to file 1099-NEC and 1099-INT forms and I'm completely lost. The deadlines are coming up quick and I'm starting to panic. I've been renting out my parents' old house since they moved to assisted living last year. It's just one property, nothing fancy. I had a guy do some major plumbing work that cost $1,200 and I paid a local bookkeeper about $800 to help set everything up. Now I need to file these 1099 forms for them. When I went to the IRS website, it says I need to sign up for this IRIS system to e-file the forms. But when I started the application, it asks for an EIN and all this business structure information. I don't have any of that! I'm just a regular person with a rental property, not a corporation or LLC. Here's where the form starts getting confusing: **Business Structure*** Select Association Church or Church Controlled Organization Corporation Credit Union Estate Federal Government Agency Indian Tribal Governments Limited Liability Corporation Limited Liability Partnership Limited Liability Single Member or Disregarded Entity Local Government Agency Non-Profit Organization Partnership Personal Service Corporation Sole Proprietorship State Government Agency Trust **Employer Identification Number (EIN)*** **Firm/Organization Legal Name*** I don't fit into any of these categories as far as I can tell! How do regular individuals who aren't set up as businesses file these 1099 forms with the IRS? The IRIS system seems to be designed only for business entities with EINs. What am I supposed to do?

Hazel Garcia

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Another option nobody mentioned: You could use a third-party service like TaxBandits to file your 1099s. They charge a fee per form but handle all the complicated stuff. I've used them for years and never had issues. They also guide you through the process if you don't have an EIN yet.

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Laila Fury

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Do they send the recipient copies too or do I have to do that part myself? And roughly how much do they charge per form?

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Hazel Garcia

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They send the forms electronically to the IRS, but they give you PDFs of the recipient copies that you need to distribute yourself. You can email these PDFs or print and mail them. Their pricing changes a bit each year, but it's usually around $3-5 per form depending on how many you're filing. Definitely worth it to avoid the headache of figuring out the IRS systems.

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Don't forget that if you're paying contractors less than $600 in a year, you don't need to file a 1099-NEC for them at all. This applies per person/entity, not total. Saved me a bunch of paperwork last year when I realized most of my small repairs didn't meet the threshold!

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Simon White

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This is good advice but don't forget 1099-INT has a much lower threshold. You need to issue those for just $10 or more of interest paid. Different form, different rules.

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One trick I've used for weird W-2 box 14 entries is to compare with coworkers. Sometimes they've already figured it out or asked HR. In my company, we had similar backslashes as separators between different benefit codes. Also check your last paystub of the year - sometimes the full descriptions appear there but get abbreviated on the W-2.

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Nora Brooks

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Never thought to check my last paystub! That's really smart. Do you know if box 14 items generally affect your tax refund amount at all?

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Most Box 14 items don't affect your federal refund - they're usually just informational. They list things that are already accounted for elsewhere or things that don't impact federal taxes. However, certain items might affect state taxes depending on where you live. For example, some states allow deductions for certain contributions that might be listed in Box 14. That's why it's worth knowing what the codes mean, especially if you have a significant amount listed there.

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Millie Long

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When I imported my W-2 into TurboTax, it automatically recognized some of the box 14 codes but had a question mark next to the backslash. Has anyone tried different tax software to see if some handle these unusual codes better than others?

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KaiEsmeralda

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I've used both H&R Block and TaxAct in different years, and neither was particularly good with unusual Box 14 entries. They both basically just let you enter the information but don't actually interpret what it means. I think it's because these codes aren't standardized.

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