Have you looked into setting this up as a family foundation instead? If you're planning to do this long-term and potentially increase the amount, it might be worth the initial setup costs. My in-laws did this for a memorial scholarship and while there was more paperwork, they got the tax deduction and maintained control.

Just wanted to add another perspective from someone who's been through this process. We started with a similar setup - wanting to maintain control while getting tax benefits for our annual $2,500 scholarship. After researching all the options mentioned here, we went with a community foundation and it's been fantastic. The key thing people don't always mention is that most community foundations will let you establish specific criteria for your scholarship (academic merit, financial need, field of study, etc.) and you can usually serve on or influence the selection committee. So while you're not writing the check directly to the student anymore, you're still very much involved in who receives it. The tax deduction has been significant for us - at our tax bracket, we're essentially getting back about 30% of what we contribute, which lets us fund a larger scholarship than we could afford otherwise. The foundation handles all the compliance stuff, tracks the recipients, and even provides updates on how the students are doing. Highly recommend this route if you want both tax benefits and meaningful involvement in the selection process.

don't forget about your cell phone expenses too! if you're using your personal phone for 1099 work you can deduct a percentage of that cost too. same principle as the internet - figure out what % is for business and deduct that part.

One thing I haven't seen mentioned yet is keeping detailed records throughout the year, not just at tax time. Since you're working from home with mixed income sources, I'd recommend setting up a simple tracking system now for 2024. I use a basic spreadsheet to log my work hours by income type (W-2 vs 1099), internet usage patterns, and any work-related calls/activities. This makes calculating business percentages much easier and gives you solid documentation if the IRS ever asks questions. Also consider whether you might benefit from quarterly estimated tax payments on your 1099 income to avoid underpayment penalties. With $4700 in side income, you might owe taxes on that portion depending on your total tax situation. The internet deduction advice others gave is spot on - you can definitely claim a reasonable percentage for your 1099 work. Just make sure whatever method you use (hours worked, income ratio, etc.) is consistent and well-documented.

Reading through everyone's experiences here has been really eye-opening! I'm dealing with a similar situation - my 2023 amended return shows "Completed" as of December 3rd, 2024, so I'm about 2 months out now. Based on what everyone is sharing, it sounds like I'm getting close to the point where I should be concerned. @Lauren Wood's breakdown of the backend processing steps after "Completed" status is incredibly helpful - I had no idea there were quality reviews, check printing queues, and mailing processes that happen after that date. The questions you provided are exactly what I'll ask if I need to call. @Evelyn Kelly definitely call that number tomorrow with those specific questions! Your October completion date puts you way past any reasonable timeframe. The success stories from @Ian Armstrong and @Miguel Ramos show that once you get the right person on the phone, they can usually track down what happened and get a replacement check issued quickly. It's frustrating how the "Completed" status is so misleading - they really should be more transparent about what that actually means vs when people can expect their refunds. This thread has been more informative than anything on the official IRS website! Thanks everyone for sharing your experiences and timelines.

I'm new to this community but facing the exact same issue! My 2023 amended return shows "Completed" as of November 8th, 2024, and still no refund check. Reading through everyone's experiences here has been incredibly helpful - way more informative than anything I could find on the official IRS website. It's really concerning how inconsistent the wait times are after the "Completed" status. Some people get their checks in 2-3 weeks while others are waiting 3+ months like @Evelyn Kelly. The fact that @Lauren Wood confirmed there are hidden backend processing steps (quality reviews, check printing queues, mailing processes) after "Completed" status really explains the confusion. @Evelyn Kelly I hope your call goes well tomorrow morning! At 3+ months past your October completion date, you definitely have grounds to push for answers. The success stories from @Ian Armstrong and @Miguel Ramos are encouraging - it sounds like once you get the right representative, they can track down what happened and get replacement checks issued quickly. I'm planning to call that same number (800-829-0582 ext 633) next week if I don't receive anything soon. Thanks to @Lauren Wood for that detailed list of questions to ask - I'm writing those down! This community knowledge is so much more valuable than the vague status updates on the official tools.

Has anyone tried just calling the mortgage company and asking what alternatives they'll accept? When I got my mortgage last year, I was missing one W2 and they said a final paystub from that year would work as a substitute. Might save you some time if they're flexible!

Just want to add another perspective as someone who went through this recently. If you're in a time crunch, I'd recommend trying multiple approaches simultaneously rather than going one by one. I started with the IRS transcript request online (which was fastest), contacted my old employers' HR departments, and also checked if I had any old tax prep files saved on my computer or email. The IRS transcripts came through in about 2 days and my lender accepted them without any issues. But having the backup requests going meant I wasn't stressed about timing. Also, pro tip - if you're working with a mortgage broker, they often have relationships with lenders who are more flexible about documentation requirements than if you go direct to a bank.

Something to consider: the tax law around this is covered in IRC section 119 and the related regulations. If the meals are provided for a "substantial noncompensatory business reason" (like security concerns you mentioned), they might actually qualify as fully non-taxable, even with the 80% discount structure. I'd suggest asking HR for their written policy on meal benefits taxation. Many non-profits haven't updated their policies to reflect recent tax court rulings that have been more favorable to employees in these situations. Having the actual policy in writing can help you identify if they're following outdated guidance.

This is a really thorough discussion! I'm dealing with a similar situation at my non-profit where they're valuing our subsidized meals way above what comparable food costs elsewhere. After reading through all these responses, I'm planning to: 1. Document local restaurant prices for similar meals (great suggestion from Carmella) 2. Request the written policy from HR using the specific IRC section 119 language Ellie mentioned 3. Calculate my actual additional tax burden to see if it's worth pursuing One question - for those who successfully got their organizations to change the policy, how long did the whole process typically take? I want to set realistic expectations before I start down this path. Also, did anyone face any pushback or retaliation for questioning the meal benefit taxation? Thanks for all the detailed advice - this community is incredibly helpful for navigating these complex tax situations!