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Ask the community...

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Chloe Davis

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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.

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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.

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Chloe Davis

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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.

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AstroAlpha

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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.

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Diego Chavez

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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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StarStrider

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Something nobody mentioned yet - make sure you keep DETAILED records if you're planning to deduct vehicle expenses. My cousin got audited because of his business vehicle deductions and it was a nightmare because he didn't have good documentation. Keep a mileage log with dates, starting/ending odometer readings, and purpose of each business trip. Take pictures of receipts for all vehicle expenses. Document when and why you're using the vehicle for business vs personal use. The tax savings can be huge but not worth it if you can't back it up during an audit!

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Zoe Stavros

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Thanks for the warning! What's the best way to track all this? Do you use an app or just write it down?

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StarStrider

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I personally use MileIQ app - it automatically tracks all my trips and lets me swipe right for business or left for personal. Super easy and creates IRS-ready reports. But there are lots of good options like Everlance or TripLog too. The important thing is consistency. The IRS loves to question vehicle deductions, so whatever method you choose, use it religiously. And if you're claiming the vehicle is used 70% for business, your records should actually show approximately that percentage. I've seen too many people claim high business use percentages without the documentation to back it up.

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Has anyone here actually formed an LLC operating agreement that specifically includes the purchase of a business vehicle? I'm wondering if I need to update my operating agreement before purchasing a truck for my landscaping business.

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Sofia Torres

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You don't necessarily need to update your operating agreement, but it's not a bad idea to document the vehicle use policy. My accountant had me create a simple resolution authorizing the vehicle purchase that we keep with our LLC records. Basically just states the business purpose of the vehicle, who's authorized to drive it, and how personal use will be handled.

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Something nobody's mentioned yet - make sure you check the updated requirements for the EV tax credit. There are new restrictions based on vehicle price, where it was manufactured, and battery component sourcing. For example, if your Tesla Model Y is over $80k, it might not qualify anyway, and the rules changed in 2023 and again in 2024. Also, if you already took delivery, you should have received a certificate from Tesla confirming the vehicle's eligibility. That's now required documentation regardless of the LLC situation.

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Thanks for bringing this up! My Model Y was $58,500 and I did receive the certificate from Tesla confirming it meets the North American assembly requirements. I also checked and the battery components meet the new criteria as well. I was more concerned about the ownership transition issue since the IRS seems pretty strict about documentation. Sounds like I need to keep all paperwork showing the transition from LLC to personal ownership, plus the dissolution documents for the LLC.

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That's great! You're definitely under the $80k limit for SUVs, and having that certificate is crucial. Just make sure when you file that you include Form 8936 (Qualified Plug-in Electric Drive Motor Vehicle Credit) with your personal tax return. One more tip - if your income is over $300,000 (joint) or $150,000 (single), the credit starts to phase out. But based on your situation, it sounds like you should be eligible for the full $7,500 as long as you document the ownership transition properly.

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Sophia Long

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Don't forget you also have the option to take the credit at point of sale starting this year rather than waiting for tax time! If you already purchased without doing this, it's too late now, but for anyone else reading this thread, it's something to consider for future EV purchases.

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Does the point of sale option work if you're financing? I thought it only applied if you're paying cash for the whole vehicle.

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Just to add something that hasn't been mentioned - check if your company offers a Non-Qualified Deferred Compensation plan. Some companies will let you defer acquisition payouts into these plans which can postpone the tax hit. The catch is you can't touch the money for a specified period (usually years) and there's some risk if the acquiring company has financial troubles. Also, if you have any capital losses this year, you could potentially sell some losing investments to offset gains, though that's probably more applicable to capital gains than ordinary income from restricted stock.

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Emma Davis

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Wouldn't deferring the compensation just delay the inevitable though? You still pay the taxes eventually, right? Is there any actual advantage beyond timing?

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Yes, you're just delaying the taxes, not eliminating them. The advantage can be significant though in certain situations. If you're currently in a high tax bracket but expect to be in a lower bracket during retirement, you could save substantially by deferring. Another benefit is tax-deferred growth - the full pre-tax amount grows for you instead of the post-tax amount. For someone near retirement or planning to move to a lower-tax state, deferral strategies can make a big difference. But you're right that it doesn't eliminate taxes, just optimizes when you pay them.

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LunarLegend

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Everyone's talking about the tax implications but nobody mentioned the withholding! When my company got acquired, they withheld at a flat 22% which wasn't enough for my tax bracket. I got absolutely destroyed the next April with a huge tax bill plus underpayment penalties. Make sure your employer is withholding enough or set aside like 35-40% of the payout for taxes depending on your bracket. Seriously, the surprise tax bill was devastating.

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Oh damn, I hadn't even thought about the withholding part. I'm definitely in a higher tax bracket than 22%. I'll check with our payroll department about this. Did your company give you any option to increase the withholding percentage?

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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.

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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.

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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!

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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.

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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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