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This is probably an unpopular opinion, but I think actually doing your taxes is the best simulator. I just use the free fillable forms on the IRS website and follow the instructions. If you mess up, the system usually catches calculation errors. My strategy: I do a "practice run" of my taxes in January before all my official forms arrive, using my best estimates. Then when I get all my real documents, I do the official version. The practice run helps me understand what deductions I should be looking for and how different scenarios might play out.
But doesn't that risk submitting incorrect information to the IRS if you make a mistake? I'd be terrified of accidentally committing tax fraud or something.
Has anyone tried UnderstandTax app? My friend recommended it - supposedly it has mini-games that teach you different aspects of tax code. One game has you sort expenses into deductible vs non-deductible piles for different scenarios (W2 employee vs 1099 contractor). Another has you calculate tax liability based on different inputs. I haven't tried it myself yet but I'm thinking about downloading it. Anyone have experience with it?
I downloaded it last month! It's actually pretty decent. The deduction sorting game helped me understand what I could write off for my side business versus my day job. They also have a tax bracket visualization tool that shows how marginal tax rates actually work (which cleared up so many misconceptions I had). The app isn't super polished but definitely helped me understand some tax concepts better than just reading about them. They have a free version with basic games and a paid version with more complex scenarios.
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Regarding your RSU situation - one strategy my wife and I use is to set up a Donor Advised Fund. Since we're also in a high tax bracket with significant RSU income, we donate appreciated shares directly to our DAF instead of cash. This gives us a double tax benefit: a deduction for the full fair market value of the shares and we avoid capital gains tax on the appreciation. You can fund it in high-income years (like when large RSU blocks vest) to bunch your deductions, then distribute the actual charitable gifts over time. This has been more impactful for our tax situation than the backdoor Roth, though we do that too.
This sounds promising! How much paperwork/maintenance is involved with a DAF? And can you recommend any specific providers? I've heard of Fidelity and Schwab having these, but not sure if there are advantages to one over another.
The paperwork is minimal - much easier than setting up a private foundation. It takes about 15-20 minutes to open online, similar to opening a brokerage account. Once it's set up, you just transfer assets in and then make grants to charities whenever you want with a few clicks. I use Fidelity Charitable because that's where my other accounts are, but Schwab and Vanguard are also excellent options. They all have similar fee structures (around 0.6% administrative fee annually plus underlying investment fees). The main difference is minimum initial contribution ($5K for Fidelity, $5K for Schwab, $25K for Vanguard) and minimum grant amounts. I'd go with whoever you already have investment accounts with for simplicity.
Don't forget to check if your spouse's employer offers a mega backdoor Roth option in their 401k plan. This would allow for additional after-tax contributions beyond the standard 401k limit (potentially up to $46,000 more depending on employer plan specifics and other contributions). Those after-tax contributions can then be converted to Roth money. Not all employers offer this, but it's worth checking if they do since your income is high enough to take advantage of it. Would give you much more tax-advantaged space than just the regular backdoor Roth IRA.
Just a quick note on this - the mega backdoor Roth requires specific plan provisions: 1) allowing after-tax contributions (not just Roth), and 2) either in-plan Roth conversions or non-hardship in-service distributions. Many plans don't have both features, especially the second one. Worth calling the 401k administrator to check though!
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11 One thing to watch out for with multiple W-2s: you might end up owing taxes even if each individual employer withheld the correct amount! This happened to me. Basically, each employer calculates withholding as if they're your only job, so they each withhold at a lower tax bracket rate. But when you combine all your income, you might jump into a higher tax bracket. The software will calculate this, but just be prepared that you might not get the refund you're expecting.
23 Omg this just happened to me! I worked 3 jobs last year and ended up owing $600 when I usually get a refund. I was so confused until the tax preparer explained this exact thing.
11 Yeah, it can be a really unpleasant surprise! One way to avoid this in future years is to fill out a new W-4 form at your current job and check the box for multiple jobs, or even request additional withholding. It's better to get a little less in each paycheck than to get hit with a big tax bill in April. It's one of those weird tax things nobody tells you about until you learn the hard way!
4 If you just have W-2s and no other complicated stuff, the IRS actually has a completely free filing option called Free File Fillable Forms. It's very basic but it works! Saved me from paying for TurboTax last year.
8 I tried using that last year and it was so confusing! No explanations of anything, and it doesn't do any calculations for you. Maybe it's fine if you know exactly what you're doing, but for beginners I really wouldn't recommend it.
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Something you might consider - what about buying the truck in December, but doing a sale-leaseback arrangement with a third party until January? That way you secure the vehicle now but technically it's not "placed in service" for your business until 2024. I'm not a tax professional, but I did something similar with some expensive manufacturing equipment a few years ago. Might be worth asking your accountant about.
Wouldn't that be considered a step transaction by the IRS though? From what I understand they look at the substance of transactions rather than just the form.
That's a valid concern about step transactions. The IRS can indeed look at the substance over form if they believe transactions were structured solely to avoid taxes. The key difference in what I suggested is that there would be a genuine business purpose - securing a specific needed asset that might not be available later. A properly structured lease with market terms that transfers actual usage rights to another party temporarily could potentially work. But you're right that it would need to be a legitimate arrangement and not just paperwork to achieve a tax outcome.
Have you considered just taking the Section 179 in 2023 but carrying forward any unused deduction amount to 2024? If your 2023 income is too low to fully utilize the deduction, the unused portion can be carried forward to future tax years. This is often overlooked but might solve your problem.
This is the correct answer right here - I don't know why no one else mentioned it! Section 179 deductions that exceed your business income can be carried forward indefinitely. So if your 2023 business income is too low to fully use the deduction, you can use the remaining amount in 2024.
Zara Khan
Just an additional tip - when you send your response to the CP 2000, make sure to include Form 1040-X (Amended Return) if you're changing anything on your original return. I learned this the hard way when my first response got rejected because I just sent a letter explaining the changes without the official form. Also, keep copies of EVERYTHING you send, and if possible, send your response via certified mail so you have proof of delivery. The IRS has been known to "lose" documentation.
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Luca Ferrari
•Do you need to send Form 1040-X even if you're just providing documentation but not actually changing any numbers on your return? My CP 2000 is just asking for proof of a deduction I already claimed.
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Zara Khan
•If you're not changing any numbers and just providing supporting documentation for what you already claimed, you typically don't need to submit Form 1040-X. Just include a clear explanation letter referencing your CP 2000 notice number along with your documentation. However, you should still use the response form that came with your CP 2000 notice to indicate whether you agree or disagree with their findings. That form is crucial for proper processing.
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Nia Davis
Has anyone had success with requesting a payment plan through the CP 2000 response? I got hit with a similar notice and owe around $3000, but there's no way I can pay that all at once right now.
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Mateo Martinez
•Yes! I just went through this. When you respond to the CP 2000, there's usually a payment options section on the response form. You can check the box indicating you can't pay in full. Once they process your response and send the final bill, you can set up an installment agreement online through the IRS website for balances under $50,000. I set mine up for $100/month and it was super easy to do online. Just make sure you actually set it up once you get the final bill - don't ignore it or they'll start collections.
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