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Ask the community...

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Something nobody has mentioned yet - you should really consider setting up an LLC before starting this job. It's not that expensive (usually under $200 depending on your state) and it gives you personal liability protection. Without an LLC, if someone gets hurt on the job or something goes wrong with the concrete work, your personal assets could be at risk. Plus it makes the tax situation cleaner since you can get an EIN and use that instead of your SSN for all the paperwork. Just my two cents after learning this lesson the hard way on a roofing project last year.

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Miguel Diaz

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Interesting point about the LLC. Is it something I can set up quickly? This job is starting in about two weeks, so I'm not sure if there's enough time. And would I need to get insurance too if I form an LLC?

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You can usually set up an LLC in just a few days in most states. Many states have online filing systems now where you complete everything electronically. Once approved, you immediately get your filing documents, then you can apply for an EIN online with the IRS and get it instantly. Yes, you absolutely should get insurance regardless of whether you form an LLC or not. At minimum, you need general liability insurance for a construction project. The LLC helps protect your personal assets, but insurance is what covers actual claims. Many general contractors won't even let you on the jobsite without proof of insurance, so check if that's required in your contract.

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CosmicCowboy

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What tax software are you guys using for filing once the project is done? I did some contracting work last year and TurboTax completely messed up my Schedule C and I ended up owing penalties.

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I switched to FreeTaxUSA last year after having issues with TurboTax. Way cheaper and handled my Schedule C and all my 1099 income perfectly. Their interface for business expenses is actually easier to use than TurboTax in my opinion.

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Mia Alvarez

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Check your transcript!!! I waited for 4 months and finally checked my transcript online and saw code 570 (additional account action pending) followed by 971 (notice issued). A week later I got a letter saying they adjusted my refund amount by $320 because I had calculated a credit wrong. 2 weeks after that I finally got my refund. The "Where's My Refund" tool was useless the entire time.

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What's the easiest way to check your transcript? I tried making an account on irs.gov but got stuck in their verification process.

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Sophia Long

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I'm having the exact same issue! Filed in February and STILL waiting for my $3,450 refund. Called the IRS twice and both times they just said "it's still processing, be patient." Like HOW much more patient can I be?! This money was supposed to help pay for my daughter's braces months ago.

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Same boat! It's absolutely wild that they can just hold onto our money indefinitely with zero explanation. Have you received any letters in the mail at all? I haven't gotten anything which makes me think they aren't actually reviewing anything specific. Just a giant backlog they're slowly working through.

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Omar Zaki

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Make sure to check if the scholarship is covering MORE than just qualified expenses. My son's "full ride" included: - Tuition (not taxed) - Books (not taxed) - Meal plan (TAXED) - Housing stipend (TAXED) - Travel allowance (TAXED) The university just sent him a lump sum for the taxable portions, which got reported on a 1099-MISC. Caught us by surprise the first year when he suddenly owed taxes as a student with "no income"! The taxable portions count as income even though he never saw the money (it went straight to his student account).

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Does the student claim this income on their own return or do the parents claim it if the student is still a dependent?

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Omar Zaki

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The student reports the taxable scholarship income on their own tax return, even if they're still your dependent. It's considered the student's income because they're the recipient of the scholarship. This can create a situation where your dependent student suddenly needs to file their own tax return, even if they don't have a job. In our case, my son had to file his own return for the taxable portion of his scholarship, while we still claimed him as a dependent on our return since we provided more than half his support.

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One thing to check - are you sure the money is actually a scholarship and not a tuition reduction? Sometimes schools call it a "scholarship" but it's technically a reduction in tuition, which has different tax implications. Look at the 1098-T box 5 (scholarships/grants) vs. box 2 (amounts billed for qualified tuition). If it's truly a scholarship and is less than or equal to qualified expenses (tuition, required fees, books for required courses), then it's tax-free. If the scholarship exceeds qualified expenses, only the excess is taxable. My kid got a "presidential scholarship" that confused us at first - turned out it was actually a tuition discount, not true scholarship money changing hands, which affected how we reported it.

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Diego Flores

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Wait this is blowing my mind. My daughter's financial aid letter says "Dean's Scholarship" but now I'm wondering if it's actually a tuition discount. How can I tell the difference? Her 1098-T is confusing me.

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How to calculate adjusted basis for non-qualified ESPP with 20% stock match - tax implications?

My husband participates in a non-qualified ESPP plan through his employer, and they provide a 20% stock match when he purchases shares (at the same price per share). I'm trying to figure out how to properly handle the tax implications, especially regarding the cost basis. The Settlement Information document shows the cost basis for both the purchased shares and the matched shares. From what I understand, we only pay tax on the matched shares (not the ones he actually purchased), but I'm confused about how to properly adjust the cost basis. I believe the adjusted basis should be the compensation income plus the acquisition cost. For the matched shares, I think the compensation income is the value when they were gifted to him, but what exactly counts as the "acquisition cost" since he didn't directly purchase these matched shares? Should I just use the Fair Market Value at the time he received them? When calculating gains/losses, would I just subtract this FMV from the proceeds? There aren't any fees listed for these transactions. There's also a Supplemental Form showing a cost basis slightly higher than the purchase price, with some gains/losses reported (both short-term and long-term losses). Since these were losses, I'm guessing there wasn't any taxation, but do I still need to adjust the basis as described above? And if there were gains instead of losses, how would I handle the adjusted basis calculation then? Nothing about these shares appears on his W-2. Any help would be greatly appreciated!

Justin Evans

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I've been an investment advisor for years and see this confusion about ESPPs all the time. Another point to consider that nobody's mentioned yet: if you're dealing with losses on these matched shares, make sure you're considering the wash sale rules if you're regularly acquiring new shares through the same ESPP. I've seen clients accidentally trigger wash sales because they sold shares at a loss while continuing to acquire new shares through their regular ESPP contributions. The IRS can be quite strict about this.

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That's a good point I hadn't considered! My husband makes ESPP purchases quarterly. If we sold some of the matched shares at a loss, would the next quarter's acquisition potentially trigger wash sale rules? Does it matter that some are directly purchased and some are matched shares, or does the IRS consider them all the same type of security?

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Justin Evans

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Yes, the next quarter's acquisition could potentially trigger the wash sale rules if it happens within 30 days before or after selling at a loss. The IRS generally considers them the same security regardless of how they were acquired (purchased directly or received as matched shares). What makes this especially tricky with ESPPs is that the acquisition date for new shares is often predetermined by the plan structure, so you can't easily avoid the 30-day window like you might with discretionary investments. Some financial advisors recommend scheduling any loss-harvesting sales carefully around your ESPP purchase calendar to avoid this issue.

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Emily Parker

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Has anyone used TurboTax to handle their ESPP reporting? I'm trying to figure out if it correctly calculates the adjusted basis for matched shares automatically or if I need to override what's on my 1099-B.

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Ezra Collins

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I used TurboTax last year and it didn't handle my ESPP correctly. The software just used whatever basis was reported on the 1099-B, which was wrong for my matched shares. I had to manually override it using the "Adjusted Basis" field and enter my own calculation. It was kind of a pain but worked once I figured it out.

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Avery Davis

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Something nobody's mentioned yet - have you checked if your company has an accountable plan? Some employers have a formal process where they don't "reimburse" expenses but will pay you for them if you follow their documentation procedure. If they do, that might be your best option. Also, see if your manager will at least provide a letter stating that the laptop is required for your job but isn't provided by the company. While it won't make it deductible, it's good documentation to have if your tax situation changes or if you're ever questioned about the purchase.

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Dyllan Nantx

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Thanks for bringing this up - I've never heard of an accountable plan before. I'll check with HR to see if we have something like this in place. That's a really good idea about getting a letter from my manager. Even if I can't deduct it now, having that documentation could be useful later on. I appreciate the advice!

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Has anyone considered just making your employer pay for it? Instead of asking nicely, try framing it as "I need a laptop for the Johnson client visit next Tuesday." Then when they say there aren't enough, say "OK so you're telling me to cancel on the client?" Put it back on them to solve the problem they created.

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This is actually solid advice. I did something similar at my old job - forced management to deal with the consequences of their own policies. They magically found budget for new equipment when client relationships were at stake.

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