I've been dealing with a similar situation and wanted to share what I learned from my CPA. The most important thing is to distinguish between a true "worthless security" and a security that was acquired at a minimal value. Based on your description, it sounds like your First Republic shares likely went through the JPMorgan acquisition process rather than becoming truly worthless. Here's what you should do: 1. **Get the facts first**: Call your broker and request the "Corporate Action Notice" for First Republic Bank from May 2023. This will tell you exactly what happened - whether you received cash, JPMorgan shares, or nothing at all. 2. **If you received ANY compensation** (even pennies): This is a regular sale transaction. Use the actual acquisition date, your original cost basis, and whatever you received as proceeds on Schedule D. 3. **For the limit order problem**: Since your shares show $4 value, set your limit price at or below the current bid price (maybe $0.01 per share). This will execute immediately and create the taxable event you need. 4. **Avoid the worthless security claim** unless you truly received zero compensation. The IRS audits these heavily, and if you received even minimal payment, it doesn't qualify. The good news is that either way, you'll be able to claim most of your $5.5k as a capital loss. The documentation from your broker will make everything clear and defensible if questioned.

I went through this exact same situation with my First Republic shares last year, and after working with my tax preparer, here's what we discovered: The key is determining what actually happened during the JPMorgan acquisition. Most retail shareholders of First Republic did receive some minimal compensation - often around $0.00-$0.50 per share - rather than having truly "worthless" securities. Since your shares still show $4 value in your account, this strongly suggests you received something in the acquisition process. Here's my recommendation: 1. **Contact your broker immediately** and ask for the "Corporate Action Statement" or "Reorganization Details" for First Republic Bank from May 1, 2023. This document will show exactly what you received. 2. **For your limit order issue**: Set your limit price at $0.01 per share (or whatever minimal amount ensures execution). Since your total position is only worth $4, this will execute immediately and give you the realized loss you need. 3. **Report it as a regular sale on Schedule D**: Use May 1, 2023 as the sale date, your original $5.5k as the cost basis, and whatever minimal amount you received as proceeds. 4. **Avoid claiming "worthless securities"** unless you truly received $0. The IRS heavily audits these claims, and if you received any compensation (even pennies), it doesn't qualify. The bottom line: You'll still be able to claim nearly your entire $5.5k loss as a capital loss, but make sure you have proper documentation from your broker first. Don't let the complexity paralyze you - this is actually a fairly straightforward transaction once you get the right paperwork.

Has anyone considered that maybe there's no tax at all? My understanding is that gifts under the annual exclusion amount don't trigger tax consequences for the recipient. When your grandfather gave it to your dad and when your dad gave it to you, if the value was under the gift tax exclusion limit each time, wouldn't that mean your basis is just the fair market value at the time you received it?

This is exactly the kind of situation where getting professional help upfront can save you major headaches later. I dealt with something similar when my aunt gave me her vintage watch collection - no receipts, no appraisals, just family pieces passed down over generations. Here's what I learned: the IRS expects you to make a "good faith effort" to establish basis, but they're reasonable when original documentation doesn't exist. I ended up working with a tax professional who helped me create a defensible basis calculation using historical gold prices, comparable sales data, and a professional appraisal. One key point - make sure you understand the holding period rules. Since these were gifts, your holding period includes the time your grandfather and father owned them, so you'll likely qualify for long-term capital gains treatment. But as others mentioned, gold jewelry is taxed as a collectible at up to 28% for long-term gains, not the lower rates for stocks. Document everything you do to establish the basis - your research, appraisals, conversations with family members, anything that shows you made a reasonable effort. This paper trail will be invaluable if you're ever questioned about your calculations.

Another strategy worth considering is a Charitable Remainder Trust (CRT) if you have any philanthropic interests. This can be particularly effective for highly appreciated farmland since you get an immediate charitable deduction, avoid capital gains tax on the sale, and receive income for life. The CRT sells the property tax-free, then pays you a percentage annually (typically 5-8%) for either a term of years or your lifetime. At the end, the remainder goes to charity. If you don't need the full value immediately and want to support causes you care about, this could provide steady income while significantly reducing your current tax burden. You could also combine this with life insurance to replace the charitable remainder for your heirs if that's a concern. The tax savings from the charitable deduction can help fund the premium payments.

Given the complexity of your situation with inherited farmland in a family trust, I'd strongly recommend getting a professional analysis before making any major decisions. Each trust structure is unique, and the tax implications can vary dramatically based on factors like the type of trust, basis step-up rules, and your specific ownership percentage. One consideration that hasn't been fully addressed is the potential impact of the Net Investment Income Tax (NIIT) on your proceeds. If your trust is subject to NIIT, you could face an additional 3.8% tax on investment income, which might influence whether distributing the property before sale or keeping it in trust is more advantageous. Also, since you mentioned all co-owners are relatives, make sure you understand how the sale will be structured. If the trust is selling the entire property as one transaction, you'll need coordination among all beneficiaries for strategies like 1031 exchanges or installment sales. The "patient" approach you mentioned is smart - rushing into a decision could cost you significantly in taxes. Consider consulting with both a trust attorney and a tax professional who specializes in agricultural property transactions to model out different scenarios before proceeding.

This has been an absolutely incredible thread to follow! As someone who's been preparing taxes for several years, I thought I knew all the tricks for credential management, but you all have opened my eyes to so many resources I never considered. I wanted to share one more angle that just occurred to me while reading through all these suggestions: if you've ever had to complete any IRS compliance reviews or participated in the Return Preparer Review Program, those documents would definitely have your PTIN. The IRS sometimes selects preparers for quality reviews, and all the correspondence and documentation from those processes would include your PTIN. Also, for anyone who's ever applied for or holds an IRS Annual Filing Season Program certificate, your PTIN would be tied to that credential as well. The AFSP program requires active PTIN status, so if you've participated in that program, the IRS definitely has your information linked together. What really impresses me about this discussion is how it shows the interconnected nature of all our professional credentials and systems. It's a great reminder that we should probably maintain a master document with all this information - not just the PTIN itself, but everywhere we've used it over the years. Thanks to everyone for turning what started as a frustrating credential recovery question into such a comprehensive resource guide. This thread should honestly be pinned as a reference for anyone dealing with similar issues!

Absolutely recommend creating a credential tracking system from day one! I learned this lesson the hard way after going through my own PTIN recovery nightmare a few years back. Here's what I wish I had done from the beginning: Create a secure password-protected document (I use a encrypted PDF) with sections for each credential - PTIN, state registrations, professional memberships, etc. For each one, I now record not just the number and expiration date, but also WHERE I've used it - which software platforms, insurance applications, professional organizations, etc. For security, I store this master document in an encrypted cloud service with two-factor authentication, plus keep a backup on an encrypted USB drive in my office safe. Never store it in regular email or unprotected cloud storage since it contains sensitive professional information. Also make it a habit to note in this document whenever you provide your PTIN somewhere new - whether it's signing up for new tax software, joining a professional group, or submitting it for CE credit. Takes 30 seconds but could save you hours later if you ever need to track it down. This thread has been such a great reminder of why systematic record-keeping matters. The collective wisdom here about all the places our credentials end up scattered is incredible - definitely worth implementing some of these tracking strategies proactively rather than reactively!

Make sure u update ur W-4 after the baby is born!! I made the mistake of not doing this and was getting way less in my paychecks than I should have. The IRS has an option specifically for reporting a new baby/dependent.

Yes, you can absolutely get back more than you paid in taxes! This is totally normal and legal through refundable tax credits. The big ones for your situation are the Earned Income Tax Credit (EITC) and Child Tax Credit. With your income around $15,000 and a baby coming, you'll likely qualify for a substantial EITC - potentially around $3,995 for one child. Plus up to $1,600 from the refundable portion of the Child Tax Credit. Since your baby will be born by December 31st, you can claim them for the entire 2024 tax year. These credits were specifically designed to help working families with lower to moderate incomes, so getting back $9,000 when you only paid in $2,700 is exactly how the system is supposed to work. The IRS calculator is accurate - you're not seeing a glitch, you're seeing the safety net in action! Just make sure to keep all your documentation and file accurately. Congratulations on your upcoming arrival!