I'm actually facing a very similar decision right now! Like you, I have a solid W-2 job but am starting to expand into multiple income streams - rental properties, consulting work, and potentially an online business. The tax complexity is growing quickly and I find myself constantly second-guessing whether I'm optimizing things correctly. What really caught my attention in your post is the part about "wasting time consulting your current EA about random ideas." I'm experiencing the exact same thing. I'll have an idea about something like cost segregation for my rental or whether I should convert my consulting income to an S-corp structure, but I never know if I'm asking the right questions or if there are even better strategies I'm not considering. The tools mentioned in other comments (like taxr.ai) seem interesting for getting some strategic insights without the full EA commitment. But I'm leaning toward your original instinct - actually learning this stuff properly so I can think strategically on my own rather than always being dependent on others. One thing I'm curious about: have you considered that having EA knowledge might actually open up new business opportunities you haven't thought of yet? Even if you don't want to do traditional tax prep, there might be consulting or advisory roles that could emerge as your businesses grow.

I was in your exact shoes about 3 years ago - fascinated by tax strategy but worried about committing to the EA path without wanting to practice professionally. I ultimately went for it and can honestly say it's been transformative for my personal tax planning. What really sold me was realizing that the EA exam doesn't just teach you tax rules - it teaches you how to think like a tax strategist. Now when I'm evaluating business decisions, I automatically consider the tax implications from multiple angles. Should I buy that equipment in December or January? How will my S-corp election affect my QBI deduction? What's the optimal way to structure a real estate investment? I can answer these questions myself instead of paying for consultations every time. The studying was intense (about 280 hours for me), but I treated it like a graduate-level course in wealth building. Every concept I learned directly applied to optimizing my own situation. The business taxation section alone saved me more than the entire cost of the program in my first year. One unexpected benefit: I now review my tax returns before my CPA files them and often catch things they miss or suggest additional strategies. It's completely changed the dynamic - instead of just hoping my accountant is doing everything possible, I'm actively collaborating on optimization. If you're truly passionate about tax strategy and plan to have multiple income streams, the knowledge compounds every single year. For someone in your situation, I'd say it's absolutely worth it.

I went through exactly this transition last year! Left my SEP open with the existing money and started a 401k when I brought on employees. One thing to watch for - make sure you properly document the termination of new contributions to the SEP (even though there's no formal closure). I kept a corporate minute in my company records noting the board decision to freeze the SEP and establish the new 401k. My accountant said this creates a clear paper trail if there's ever a question about why we stopped SEP contributions for the business.

Great question! I actually went through a similar transition when my consulting business grew. You're on the right track - you can absolutely leave your existing SEP IRA open with the current funds and simply stop making new contributions when you switch to the 401(k) plan. Since you'll have employees in 2025, continuing SEP contributions would require you to contribute the same percentage for all eligible employees, which gets expensive fast. The 401(k) route gives you much more flexibility with different contribution levels and employee matching options. One practical tip: when you set up the new 401(k), check if the plan allows incoming rollovers from IRAs. If so, you might want to roll your SEP funds into the 401(k) to consolidate everything in one place. This can also help if you ever want to do backdoor Roth conversions later, since having money in traditional IRAs complicates that strategy due to the pro-rata rule. The transition timing is perfect since you're doing it at the start of a new tax year. Just make sure your 401(k) plan document is properly drafted to handle the contribution types you want (employee deferrals, employer matching, profit sharing, etc.).

Has anyone considered that maybe you don't need to report it at all? Like if the amounts were really small and Robinhood didn't think it was worth including on a 1099?

I went through this exact same situation last year with Robinhood and crypto reporting. Here's what I learned from my experience: First, you're absolutely required to report ALL crypto transactions regardless of whether they appear on your 1099 or not. The IRS is very clear about this - even small amounts need to be reported. What worked for me was downloading my complete transaction history from Robinhood (it's under Documents > Tax Documents > Cryptocurrency). Even though it wasn't on my 1099, the detailed transaction report was there with all my buy/sell data including dates, amounts, and prices. I then used Form 8949 to report each transaction individually. Yes, it's tedious if you made a lot of trades, but it's the most accurate way. For each transaction, you'll need: - Date acquired - Date sold - Proceeds (sale price) - Cost basis (purchase price + any fees) - Gain or loss The key thing I discovered is that you need to be very careful about wash sale rules with crypto - unlike stocks, these still apply and can affect your calculations. If you made dozens of transactions, honestly consider using a crypto tax service like some others mentioned. The time savings and accuracy improvement is worth it, and most integrate well with tax software like FreeTaxUSA. Don't risk ignoring it - the IRS specifically asks about virtual currency on the main tax form now, so they're definitely paying attention to this area.

Based on your situation, here are a few key points that might help with your Form 4684: Since you mentioned you've never filed a tax return before, you'll want to be extra careful with documentation. The IRS tends to scrutinize first-time filers more closely, especially for significant deductions like casualty losses. For the fair market value calculation, your $27k repair cost is actually a solid starting point. The IRS Publication 547 specifically mentions that repair costs can be used as evidence of decreased fair market value, as long as the repairs only restore the property to its pre-damage condition (which sounds like your case with the roof). One important thing others haven't mentioned - make sure you get a copy of the official FEMA disaster declaration for your area. You'll need the disaster declaration number for your Form 4684, and having this documentation helps establish that your loss qualifies for the special disaster provisions. Also, since your income is $110k, definitely run the numbers on claiming this loss on your 2023 return (amended) versus your 2024 return. If your 2023 income was lower, the 10% AGI threshold would be smaller, potentially giving you a larger deduction. Don't forget to keep detailed records of everything - the IRS has up to 3 years to audit casualty loss claims, and disaster-related deductions sometimes get extra scrutiny.

Just wanted to add a few practical tips from my own experience dealing with hurricane damage and Form 4684: Make sure to document the timeline carefully - note the exact date of the hurricane and when you discovered/assessed the damage. The IRS wants to see that the loss occurred in a specific tax year for timing purposes. Since you mentioned not having insurance, you'll want to be prepared to explain why on Form 4684 if asked. Sometimes the IRS questions why someone didn't have coverage, especially for significant losses. Just be honest about your situation. For the $27k in repair costs, try to break down the invoices by category if possible (materials, labor, permits, etc.). This level of detail can be helpful if you face any questions later. Also, if any of the work required permits from your local building department, keep copies of those as well - they help establish that the repairs were necessary and legitimate. One thing that helped me was creating a simple timeline document with photos, receipts, and key dates all organized chronologically. It made filling out Form 4684 much easier and gave me confidence that I had everything properly documented. Since this is your first time filing, definitely consider using tax software that specifically handles casualty losses or working with a tax professional. The rules are complex enough that it's worth getting it right the first time.

Has anyone just printed out Form 4684 and done it manually? You can still e-file the rest of your return through TurboTax and just mail in the 4684 separately with a 1040-X later when it becomes available. That's what I did last year with a delayed schedule.

I'm dealing with this exact same Form 4684 issue right now! Based on all the suggestions here, it sounds like there are several viable paths forward. For those considering the professional software route that Freya mentioned - I actually called Drake Software yesterday and they confirmed Form 4684 is fully available in their system. The rep said they prioritize getting all forms ready by mid-January since tax professionals can't afford to wait. One thing I'm curious about - has anyone tried contacting TurboTax directly to see if they'll extend your subscription to next year as compensation for this delay? Seems like they should offer something for the inconvenience, especially for long-time customers like the original poster. Also wanted to mention that if you do decide to switch software mid-stream, make sure to keep detailed records of what you've already entered. Even if the new software can't import your TurboTax file, having everything organized will make the re-entry process much faster.