I switched from W-2 to 1099 last year and heres what surprised me the most: QUARTERLY ESTIMATED TAX PAYMENTS!! You have to basically be your own payroll department and send tax payments 4 times a year. If you dont you can get hit with penalties. Plus theres the whole self-employment tax thing which is like 15% on top of regular income tax. And health insurance is crazy expensive when you have to buy it yourself instead of getting it thru an employer. Unless theyre offering you at least 30% more per hour, stick with the W-2 job!!

As someone who recently went through this exact decision process, I can't stress enough how important it is to run the actual numbers. Based on what you've described - $23/hour W-2 vs $21/hour 1099 - this would be a significant pay cut once you factor in all the additional costs. Here's what I wish someone had told me: With 1099 work, you'll pay an extra 7.65% in self-employment taxes (the employer portion), plus you'll lose the automatic withholding safety net. You'll need to make quarterly estimated tax payments or face penalties. And don't forget about health insurance - if your current W-2 job offers benefits, replacing those on your own can cost $300-600+ per month. The remote work aspect is tempting, but at only 150 guaranteed hours, you're looking at maximum monthly income of $3,150 before taxes (and potentially much less in slow months). Your current position at $23/hour for full-time work gives you more income stability and better take-home pay after all expenses. I'd recommend asking the new company if they can match or exceed your current W-2 compensation when adjusted for the 1099 structure - that would probably need to be around $30/hour to break even financially.

One option nobody's mentioned - you could ask the executor to set aside a reasonable reserve for potential tax liabilities (maybe 15-20% of the newly discovered assets) and distribute the rest now. That's what we did with my grandfather's estate when we found an old stock account two years after he passed.

Has the executor filed Form 706 (estate tax return) already? If the estate is under the federal exemption amount (which is over $13 million for 2025), and Form 706 has already been filed and accepted, the ongoing income tax returns should just be for income generated by estate assets, not for the decedent's assets themselves.

Have you considered forming an LLC for your delivery gig? I did that last year for my UberEats side hustle and it changed how the income is taxed. You still pay some taxes but there are way more deductions available.

Quick tip from someone who does lots of food delivery: don't forget to track your MILES! Even on a bike, you can deduct $0.22/mile for 2024 (non-motorized rate). For car deliveries its $0.67/mile. This usually works out much better than tracking actual expenses for most people.

Back in 2022, I had a similar situation with a PCS move and refund timing. I learned that while many prepaid cards like Dasher Direct advertise "early deposits," it's not guaranteed for tax refunds. The IRS batch processing system doesn't work like regular direct deposits. In my case and for most military families I know, refunds typically hit Dasher 0-24 hours before the DDD, but I've seen some arrive right on the date. My advice from going through three PCS moves: always assume it will arrive on the exact DDD and consider any early arrival a bonus. The last thing you need during a move is financial stress!

As someone who's used Dasher Direct for tax refunds the past two years, I can share my experience. My 2023 refund had a DDD of 3/8 and actually hit my Dasher account on 3/7 around 2 PM - so about 22 hours early. But my 2022 refund with a DDD of 2/24 didn't show up until exactly 2/24 at around 8 AM. So it's really inconsistent, even with the same bank/card. Since you're dealing with PCS timing, I'd definitely echo what others said about planning for the actual DDD date. Military moves have enough moving parts without adding the stress of uncertain deposit timing. Have you considered setting up account notifications so you'll know immediately when it hits? That might give you a little more flexibility in your planning without having to constantly check your balance. Good luck with your move and thanks for your service!

Question for anyone who might know - my situation is slightly different. I'm on disability but also worked part-time for about 3 months last year (very limited hours). Would this help or hurt my chances of getting the child tax credit for my 2 year old?

I want to share some encouragement as someone who's been in a similar situation. I'm also a single parent on disability, and I was so confused about taxes when my daughter was born. It took me way too long to realize I could still file and claim credits even without traditional employment income. The most important thing to remember is that you absolutely should file a tax return! Even if your disability benefits aren't taxable (which depends on whether you receive SSI or SSDI and your total income), filing allows you to claim the Child Tax Credit which could result in a refund of up to $2,000 for your son. Don't let the paperwork intimidate you - there are free filing options available, and many are designed to handle situations exactly like yours. The IRS Free File program is a good place to start. You'll need your Social Security number, your son's SSN, and any tax documents related to your disability payments (like a 1099 if you receive SSDI). One thing that really helped me was keeping simple records - just a folder with any tax-related mail I received throughout the year. It made filing much easier when the time came. You're doing an amazing job caring for your little one, and this extra financial support through the tax system is there specifically to help families like yours. Don't hesitate to take advantage of it!