Has anyone used TurboTax for reporting regular options trading? I tried last year and it seemed to get confused with my LEAP options that crossed tax years.

Your strategy should indeed qualify each option for long-term capital gains treatment since you're holding each individual contract for over 12 months. The monthly cycling doesn't change the tax treatment of each position - the IRS looks at each option contract separately. However, I'd recommend keeping detailed records of your purchase and sale dates for each option, especially since you're dealing with LEAPs that cross multiple tax years. Make sure your broker is correctly reporting the holding periods on your 1099-B forms. One additional consideration: while 12 trades per year is unlikely to trigger trader status, you might want to document that this is an investment strategy rather than a business activity. Keep records showing this is part of your investment portfolio management rather than your primary source of income or a daily trading business. The 15% long-term capital gains rate you mentioned applies if your total taxable income falls within the 15% bracket range. Higher income levels face 20% long-term capital gains rates, so make sure you're planning for the correct rate based on your overall tax situation.

Don't forget to contact the IRS directly to flag this for them BEFORE you file taxes this year! We had a similar issue and filed our taxes normally, then got audited because someone else had already claimed education credits using the fraudulent 1098-T. Complete nightmare. File Form 14039 (Identity Theft Affidavit) ASAP.

This is definitely a red flag for identity theft, and I'm glad you're taking it seriously. In addition to all the excellent advice already given, I'd recommend your uncle also contact the Social Security Administration to report potential misuse of his SSN. They can place a fraud alert on his Social Security number which adds another layer of protection. Also, when you call Westfield State tomorrow, ask to speak with both their registrar AND their compliance/fraud department if they have one. Universities are required to have procedures for handling identity theft cases involving financial aid, so they should have a clear process to follow. Make sure to get everything in writing - ask them to email you confirmation of your conversation and what steps they're taking to investigate. One more thing - your uncle should consider signing up for IRS Identity Protection PIN (IP PIN) program once this is resolved. It's a free service that gives him a unique PIN each year that must be used when filing his tax return, which prevents fraudulent returns from being filed under his SSN.

Wait, I think everyone is confusing two separate issues here. As a fellow indie contractor, let me clarify: 1) Line 18 on Form 1040 is where WITHHOLDING appears, not your tax liability. Of course this is zero for you - nobody withholds taxes from your contractor payments. 2) The actual income tax you owe appears on line 16 of Form 1040. This amount should NOT be zero unless you have other credits offsetting it. The Form 8880 credit is limited to your income tax liability, not your SE tax. So if your income tax on line 16 is actually zero after all deductions and other credits, then yes, you can't use the Saver's Credit. Check your line 16 amount before the Form 8880 credit is applied - that's your limiting factor.

This thread has been incredibly helpful! I'm also an independent contractor and was making the same mistake as the original poster - looking at line 18 instead of understanding the actual tax liability limitation. After reading through all the responses, I realize my situation is that my income tax liability (line 16) gets reduced to zero by the child tax credit, which means there's no income tax left for the Form 8880 credit to offset. It's frustrating because I'm paying plenty in self-employment taxes, but those don't count for this particular credit. For anyone else in a similar situation, it might be worth looking at whether you can adjust your retirement contribution timing or amounts to optimize between the different credits available. Sometimes spreading contributions across tax years can help maximize the total tax benefits you receive.

17 Has anyone used TurboTax Self-Employed for filing both 1099-NEC and 1099-MISC income? Is it worth the extra cost compared to the regular version?

Welcome to the 1099 world! As someone who made the same transition a few years ago, I can tell you that yes, you absolutely need to file a tax return even though you've been making quarterly payments. Those quarterly payments are essentially just prepayments toward your actual tax liability that gets calculated when you file. Here's what I wish someone had told me when I started: your quarterly payments are estimates based on what you think you'll owe, but your actual tax liability is determined by your real income and deductions when you file Form 1040 with Schedule C attached. If you overpaid through quarterlies, you'll get a refund. If you underpaid, you'll owe the difference (plus potential penalties if it's significant). For your 1099-MISC income from surveys and online platforms, it should be included in your quarterly estimates since it's all self-employment income subject to both income tax and self-employment tax. When filing, you'll report everything together unless the activities are completely unrelated businesses. My advice: start organizing all your business expenses now (home office, internet, phone, software, supplies, etc.) because these deductions can really add up and reduce your tax liability. And consider using tax software designed for self-employed folks - it's usually worth the extra cost for the guidance on deductions you might miss.

One thing nobody's mentioned yet - if part of the inheritance is coming from a LIFE INSURANCE policy, that's typically tax-free even if it's a large amount. Just make sure you don't confuse annuities (which can be taxable) with life insurance death benefits (which usually aren't). My family got really confused about this distinction when my grandfather passed.

Great question! You're absolutely right to be confused because there's a lot of misinformation floating around about inheritance taxes. The good news is that for most people, inherited money is NOT subject to federal income tax. Here's what you need to know for your $260K inheritance: 1. **No federal income tax**: As the beneficiary, you won't pay income tax on the $260K itself. This is true whether you take it as a lump sum or installments. 2. **Estate tax threshold**: The federal estate tax only kicks in for estates over $13.61 million in 2024 (and $13.99 million in 2025), so unless grandma's total estate was massive, no estate tax was owed either. 3. **State considerations**: A few states do have inheritance taxes that beneficiaries pay, but most don't. Check your state's rules to be sure. 4. **What IS taxable**: Any income you earn FROM the inheritance (like interest, dividends, or rental income if you invest it) will be taxable going forward. 5. **Special cases**: If any portion comes from retirement accounts like traditional IRAs or 401(k)s, those distributions would be taxable as income to you. The family members insisting you'll owe taxes might be thinking of other situations or confusing inheritance with other types of income. For a straightforward cash inheritance like yours, you should be in the clear!