Coming from someone who's been in the tax industry for over a decade, I'd strongly recommend going straight for the EA if you're serious about advancing your career. The CRTP might seem like an easier entry point, but it's really limiting your potential right from the start. Here's what I wish someone had told me early on: the EA exam isn't as scary as it seems, especially with your bookkeeping background. You already understand basic accounting principles, which gives you a huge advantage. The three-part structure means you can tackle it piece by piece rather than one massive exam. Given that you're considering a move to Oregon, the EA is a no-brainer. California-specific credentials won't help you there, and you'd essentially be starting over. Plus, even if you stay in California, EA status commands more respect and higher fees than CRTP. My advice? Skip the CRTP entirely, invest in good EA exam prep materials, and dedicate 4-6 months to serious study. The return on investment is so much better long-term. You'll thank yourself later when you're charging $150+ per hour for representation work instead of being stuck at basic prep rates.

As someone who recently went through this exact decision process, I wanted to share my perspective. I ultimately chose the EA route and couldn't be happier with that choice. The key factor for me was scalability. With a CRTP, you're essentially locked into California and limited to basic tax preparation. The EA opens doors not just geographically, but professionally - you can handle complex tax issues, represent clients before the IRS, and command significantly higher fees. Since you mentioned possibly relocating to Oregon, that alone should push you toward the EA. I have colleagues who started with state-specific credentials and later regretted having to essentially restart their certification journey when they moved. From a practical standpoint, the EA exam is challenging but very doable with your bookkeeping background. The three-part structure actually makes it less overwhelming than it initially appears. I used a combination of Gleim for structured learning and supplemented with additional practice questions from other sources. One thing that really helped me was connecting with local EA study groups through the National Association of Enrolled Agents. Having that peer support made a huge difference, especially when tackling the more complex business taxation concepts. Bottom line: if you're serious about advancing in the tax field, go straight for the EA. The time and money investment pays off much faster than taking the incremental CRTP route.

Just FYI as a tax preparer, bring ALL your medical receipts to your appointment, not just COBRA. Many people forget about mileage to medical appointments (17 cents per mile for 2024), prescription costs, dental expenses, eye care, medical equipment, etc. Every dollar helps get you closer to that 7.5% threshold.

Great question about COBRA and taxes! Just wanted to add one important point that might help you save money - if you have any self-employment income from your freelance work, you might qualify for the self-employed health insurance deduction for your COBRA premiums. This is WAY better than the itemized medical expense deduction because it's an above-the-line deduction (meaning it reduces your AGI directly) and you can still take the standard deduction. Since you mentioned having 1099 income, definitely ask your tax preparer about this. The self-employed health insurance deduction lets you deduct health insurance premiums (including COBRA) as long as you have net self-employment income and you're not eligible for coverage through your spouse's employer plan. Given that you're both on COBRA, this could be a huge tax saver. For documentation, bring your 1099s showing the freelance income and all your COBRA payment records. The preparer can determine if this applies to your situation - it could potentially save you way more than trying to meet that 7.5% AGI threshold for itemized medical expenses!

I went through this exact situation with my grandmother's estate last year. She made a substantial gift to family members in March and passed away in September of the same year. After consulting with our estate attorney, we were advised that both forms are indeed required. The Form 709 establishes the gift and its valuation at the time it was made, while the Form 706 includes it under the 3-year rule for estate tax purposes. One thing that really helped us was getting the property appraised as of the gift date (April 2023 in your case) rather than the date of death. This established the fair market value for gift tax purposes. The attorney explained that having this documentation upfront made both filings much smoother and helped avoid any IRS questions later. Also, make sure you're aware of the filing deadlines - Form 709 is typically due by April 15th of the year following the gift, and Form 706 is due 9 months after death (with possible extensions). Since your mom passed in October 2023, you'll want to coordinate the timing of both filings carefully.

I'm dealing with a very similar situation right now with my father's estate. He gifted some stocks to my brother and me in June 2023, and then passed away unexpectedly in December of the same year. From what I've learned through this process, you definitely need to file both returns. The Form 709 is required because the gift was completed during your mom's lifetime - the deed transfer made it a legal gift that needs to be reported. Then on Form 706, you'll include it in Schedule G as a transfer within 3 years of death. One thing I wish I'd known earlier: get organized with your documentation now. You'll need the original deed, any appraisals, and records of your mom's original cost basis for the property. The IRS may want to see how you determined the fair market value on the gift date versus any estate valuation. Also, don't stress too much about the "double reporting" - as others mentioned, the unified credit system prevents actual double taxation. It's really more about proper documentation and ensuring the IRS can track all transfers that affect the estate tax calculation. Have you already started gathering the necessary paperwork? That's honestly been the most time-consuming part for me.

Has anyone actually been audited about disaster withdrawals? I took one last year but didn't keep great records and now I'm worried.

I went through this exact situation after Hurricane Ian hit Florida. The key thing to understand is that while your employer may not require documentation upfront, the IRS absolutely will want proof if they decide to review your return. Here's what I learned the hard way: start documenting everything NOW, even if you think you don't need it. Take photos of all damage, save every receipt related to repairs or temporary housing, and get your FEMA disaster declaration number for your area. You'll need this specific number when filing your taxes. The good news is that FEMA-related 401k withdrawals are generally treated favorably by the IRS if properly documented. You won't pay the 10% early withdrawal penalty, but you will still owe regular income tax on the amount (unless you qualify to spread it over 3 years). One thing that really helped me was creating a dedicated folder - physical and digital - for all disaster-related documents. Include your withdrawal paperwork, damage photos, contractor estimates, insurance correspondence, and any FEMA communications. This saved me when the IRS sent a letter asking for verification about 8 months after I filed. Don't let the documentation worry stop you from getting the help you need right now. Just be proactive about keeping records as you go through the recovery process.

This discussion has been incredibly helpful! As someone new to capital gains planning, I had the same misconception that many others seem to have had - thinking that only my W-2 income counted toward the threshold calculation. Reading through everyone's experiences, I realize I need to be much more systematic about tracking my investment income throughout the year. I've been holding some Apple and Google stocks for about 3 years now, and I was thinking about selling some to rebalance my portfolio. But I never considered how the dividends I've been receiving would affect my available space in the 0% bracket. The "bucket filling" analogy that @Taylor To used really clicked for me - it makes so much more sense now that capital gains stack on TOP of your regular income rather than being calculated separately. And @Admin_Masters' real-world example with the quarterly dividends reducing available space by so much is exactly the kind of detail that helps me understand the practical implications. I'm going to set up a tracking system similar to what @Lukas Fitzgerald described to monitor my total taxable income throughout 2025. Better to plan this properly now than get surprised at tax time next year! Quick question for the group - for someone just starting this kind of tax planning, would you recommend focusing on the federal brackets first and then worrying about state taxes, or should I be considering both from the beginning? I'm in Texas so no state income tax, but I want to make sure I'm not missing anything important in my planning approach.

This has been such an enlightening thread! I've been lurking in this community for a while but finally created an account because this discussion clarified so many misconceptions I had about capital gains taxation. Like many others here, I was completely wrong about how the 0% bracket works. I thought my salary income and capital gains were calculated separately, so I was planning to sell a large chunk of my Tesla stock (held since 2019) thinking I'd pay 0% since my regular income is only $41,000. Now I understand that the capital gains would stack on top of that income, potentially pushing me into the 15% bracket much faster than expected. The tracking spreadsheet idea that several people mentioned is brilliant - I'm definitely implementing that starting this month. I've been receiving quarterly dividends from my index funds without really thinking about how they impact my tax planning. After reading @Admin_Masters' example about $2,800 in dividends reducing available 0% space so significantly, I went back and calculated my own dividends for this year. Turns out I've already received about $1,900 in qualified dividends, which leaves me with much less room than I thought! One question for the group: when you're planning these strategic sales, do you typically sell your highest-gain positions first (to maximize the benefit of the 0% rate), or do you focus more on rebalancing your portfolio and sell whatever makes sense from an investment perspective? I'm trying to figure out the best approach for managing both tax efficiency and portfolio allocation goals. Thanks to everyone who shared their experiences - this is exactly why I love this community!