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Another option you might want to consider is a Charitable Remainder Trust (CRT). You contribute the appreciated asset to the trust, get an immediate partial tax deduction, and the trust sells the asset tax-free. The trust then pays you an income stream for life or a set period, and the remainder goes to charity when the trust ends. The math can work out quite well if you're planning to hold the asset long-term anyway. I did this with some tech stocks that had appreciated 1000% and it saved me a ton in capital gains while providing steady income.
Would this work for crypto? I've got some ETH that's gone up like crazy and I'm trying to figure out how to cash some out without giving half to Uncle Sam.
Yes, it can work for cryptocurrency. The key is that the trust sells it after you've donated it, so the trust itself doesn't pay capital gains tax on the appreciation. You'll need to find a trustee comfortable with handling crypto assets though, as some traditional trustees aren't familiar with the process. Keep in mind that you're ultimately giving a portion to charity - this isn't a strategy to avoid taxes completely while keeping all the money. But the tax benefits plus the income stream can make the math very favorable compared to just selling and paying capital gains tax directly.
Has anyone actually tried the S-Corp to Wyoming LLC to trust strategy the OP mentioned? I've heard claims that Wyoming entities provide strong asset protection, but I'm skeptical about the tax benefits. Seems like the IRS would see through this pretty quickly.
I looked into something similar for my business. The Wyoming LLC part can work for privacy and some liability protection, but it doesn't magically change your tax situation. The IRS follows the money regardless of how many entities you put in between. And trying to loan yourself money through your own entities gets really tricky really fast.
Something nobody has mentioned yet - you should check if your partner's plan is better than what your new job offers! Often workplace insurance plans vary DRAMATICALLY in quality, coverage, and cost. My husband's plan has a $500 deductible while mine was $3,000. We saved over $2,000 last year by putting me on his plan even though we had to pay extra for it. Even if you're allowed to stay on your partner's plan, it might not be the best financial choice depending on the details of both plans. Also consider that your job is temporary - if you take their insurance, what happens after 5 months? Would there be a gap before you could get back on your partner's plan? These practical considerations are just as important as the tax implications.
That's a really good point I hadn't considered! The job is offering a high-deductible plan ($2,750) while my partner's plan has a $1,000 deductible. And you're right about the gap - I'm not sure if there would be a waiting period to get back on his insurance after my job ends. Do you know if special enrollment periods apply when you lose job-based coverage?
Yes, losing job-based coverage does qualify as a special enrollment event that would allow you to join your partner's plan outside the normal enrollment period. You typically have 30 days from the loss of coverage to request enrollment in the new plan. As for the deductible difference, that's definitely something to consider carefully. Also look at the premium costs - what would your employer charge versus what your partner's paycheck deduction would be for adding you? Sometimes the premium difference can outweigh the deductible savings. And don't forget to compare the networks - make sure your doctors are covered in both plans before making a decision.
One thing to consider - if your temporary job is W-2 employment, you'll have taxes withheld automatically. But if it's 1099 contract work (which many temporary positions are), you'll need to set aside money for taxes yourself. At your income level jumping up suddenly, you might be surprised by how much you'll owe next year. Also, the $5,050 dependent limit for 2024 is for gross income. If your job is 1099, you can deduct legitimate business expenses which might keep your net income under the limit.
I actually built my own Excel spreadsheet to handle this exact situation. The key is to understand that with Section 1250 property, you have to count the actual months, but the month of disposal only counts as half a month. So for your example: Property placed in service in May, sold in February. If it was mid-month convention and straight-line: - In the year of sale: count January (1) + half of February (0.5) = 1.5 months - So you'd take (annual depreciation รท 12 ร 1.5) for your final year amount Happy to share my spreadsheet if anyone wants it.
Would love to see that spreadsheet! Does it handle different recovery periods (27.5 vs 39 year) and mid-quarter convention too?
Yes, it handles both 27.5 and 39-year recovery periods for real property. It also has a section for mid-quarter convention that I use for equipment and other business assets. I designed it to be pretty flexible where you just input the property type, cost basis, placed in service date, and disposal date. It automatically determines the right convention and calculates both the regular annual depreciation and any partial year amounts. I've found it matches up with what my accountant calculates manually.
Has anyone here tried using the IRS's own depreciation worksheet in Publication 946? I know it's not as convenient as an online calculator, but it does walk you through all the different conventions and how to handle dispositions during the year. It's a bit tedious but at least you know it's following the exact IRS rules. I think the example on page 47 (or somewhere around there) specifically covers selling property before its anniversary date.
I went through this exact situation last year! My university also misclassified me as a nonresident when I had clearly passed the substantial presence test. What I did in FreeTaxUSA: 1. Made sure to select "resident alien" filing status at the beginning 2. Entered my W-2 information normally 3. Added my scholarship income as "Other Income" in Schedule 1 4. For the withholding, I added it in the "Federal income tax withheld" section I got a pretty decent refund and had no issues with the IRS. The most important thing is making sure you're filing as a resident alien and not using the 1040-NR form.
Thank you for the detailed steps! Did you have to do anything special for the state tax portion or was it pretty straightforward once you figured out the federal part?
The state part was actually pretty simple once I figured out the federal portion. I just entered the state withholding amount from my 1042-S in the state withholding section along with my W-2 state withholding. For the income, I reported it the same way on my state return as I did on my federal. FreeTaxUSA walks you through the state portion after you complete the federal section, and the state return automatically imports most of the information from your federal return. Just make sure to double-check that all the withholding amounts are correct before submitting.
One important thing to check is if you have a tax treaty with your home country! I'm from India and we have a tax treaty with the US that makes some scholarship money exempt from taxes. Even as a resident alien, you might still qualify for certain treaty benefits. FreeTaxUSA doesn't handle tax treaties well, which might be why you're struggling to find where to enter the 1042-S. If you do have treaty benefits, you might need to use a different software like TaxAct or go to a professional.
This is incorrect advice. As a resident alien, you generally CANNOT claim tax treaty benefits. Those are mostly for nonresident aliens only. Once you become a resident for tax purposes, you lose most treaty benefits except for very specific exceptions.
You're right, I should have been more clear. Most tax treaty benefits are for nonresident aliens, but there are some specific provisions that continue to apply even after you become a resident alien. It depends entirely on the specific treaty and the specific type of income. For example, the US-China treaty has provisions for students that can continue for a limited time even after becoming a resident alien. But you're correct that in most cases, becoming a resident alien means losing treaty benefits.
Andre Laurent
Don't cash that check yet! This happened to my brother last year. Turns out the IRS system had somehow duplicated his return and processed it twice - once correctly showing that he owed money, and once incorrectly showing a refund. When he called, they told him to return the check with a letter explaining the situation. He sent it back certified mail with a copy of his original tax return. About a month later, they withdrew the correct amount from his account. The IRS rep said if he had cashed the erroneous refund check, they would have eventually caught it and he'd owe interest and possibly penalties.
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AstroAce
โขHow do you return an IRS check properly? Do you just write "VOID" on it and mail it back, or is there a specific process to follow?
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Andre Laurent
โขThere's a specific process. You should mail the check back to the IRS location listed in the instructions that came with it (or if no instructions, to the IRS office that services your area). Include a brief letter explaining why you're returning it. Don't write VOID on the check - send it back uncashed exactly as you received it. Include your taxpayer info (name, address, SSN) and phone number in your letter. Send it certified mail so you have proof you returned it. The IRS website has instructions for returning erroneous refunds - search for "returning erroneous refund" on IRS.gov.
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Zoe Kyriakidou
Check your tax transcript ASAP! You can access it online at IRS.gov by setting up an account. The transcript will show exactly what happened with your return and why they issued a refund. Most likely explanations: 1) The IRS made a mistake in processing 2) You had credits/payments you weren't aware of 3) Your return had a calculation error the IRS corrected 4) They processed an amended return you didn't file (identity theft risk) If it's #4, you need to contact the IRS fraud department immediately. Had this happen to a client of mine - someone filed a fake amended return in their name.
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Jamal Brown
โขI second this! Transcript is the fastest way to see what's happening. My cousin got a surprise refund last year, and the transcript showed someone had filed an amended return with her info. Turned out to be identity theft.
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