Isn't it interesting how we all have different experiences with the same system? Most credit unions release funds as soon as they receive notification, while traditional banks often hold until the official date. Have you checked if your bank has a specific policy for government deposits? Community wisdom suggests calling your bank directly if the deposit doesn't arrive within 24 hours of your DD date. They can see pending deposits before they post to your account.

Same DD date here (2/22)! I'm with a local credit union and nothing yet as of this morning, but based on what everyone's sharing, it sounds like it could hit anytime between today and Thursday. Really helpful to see the variety of experiences - some getting it exactly on the date, others a day or two later. I'll keep checking throughout the day and update if mine comes through. Thanks for asking this question, @Jayden Reed - was wondering the same thing myself!

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.

One thing no one has mentioned - make sure you file in the right order! Start with the oldest year first and work forward. This is important because some tax attributes carry forward from year to year. If you have any business losses, capital losses, or credits that might carry forward, filing out of sequence can really mess things up.

Really glad to hear you're getting your life back on track! Six years of unfiled returns might seem overwhelming, but it's absolutely manageable and you're taking the right step by addressing it now. A few key points to keep in mind: Since you mentioned having steady W-2 income with proper withholding, there's a good chance you may have been owed refunds for some of those years (though you can only claim refunds for the last 3 years). The penalty situation might not be as bad as you think if you don't actually owe much. Before jumping into anything, I'd suggest requesting wage and income transcripts from the IRS for each of those years - you can do this online at IRS.gov. This will show you exactly what income the IRS has on file for you and help you gather any missing documents. It's free and can really help you understand your situation before you start filing. Given your income level and the fact that you had withholding, you might be able to handle some of the simpler years yourself using tax software for prior years, but definitely consider getting professional help for at least the first year to make sure you're doing everything correctly. The peace of mind is worth it, and they can often spot opportunities for penalty abatements or other relief you might not know about. You've got this! Taking action now is the hardest part, and it sounds like you're in a much better place to handle it than you were before.

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.