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.

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.

Has anyone else noticed the OIC pre-qualifier seems ridiculously strict? I got rejected automatically too because of a tiny 401k, but when I actually applied for an OIC with help from my accountant, I got approved! The pre-qualifier is just a basic screening tool and doesn't consider all the factors a real IRS employee would.

The key thing to understand is that the OIC pre-qualifier is essentially a basic screening tool that doesn't capture the full picture of your situation. At 52 with only $16k in retirement savings, you're actually in a much better position than the pre-qualifier suggests. Here's what I'd recommend: Don't let the pre-qualifier rejection discourage you from pursuing an actual OIC application. The IRS will consider several factors that the online tool doesn't account for: 1) Your age (52 is definitely a factor in your favor) 2) Whether this is your only retirement savings 3) Your future earning potential 4) The age of your tax debt (2011 is getting close to the 10-year collection statute) Given that your debt will be around $6,300 after your refund is applied, and you have $16k in retirement savings, the math might actually work in your favor for an OIC. The IRS typically values retirement accounts at 80% of current value for collection purposes, so they'd see about $12,800 in available funds. However, they also consider that forcing you to liquidate your only retirement savings at 52 creates a genuine hardship. I'd strongly suggest working with a tax professional who can help you document your financial situation properly and present a compelling case for why preserving your retirement funds serves both your interests and the government's long-term collection interests.

Anybody know if there are penalties for filing Form 5500-EZ late? If the IRS is delaying releasing the forms, will they extend the deadline?

I've been in the same boat waiting for the 2023 Form 5500-EZ! Based on what others have shared here, it sounds like we have a few solid options while we wait for the paper form to be released by the end of February. I'm leaning toward trying the electronic filing route since it's already available and seems more reliable than waiting. The EFAST2 system being free (even if a bit clunky) is appealing, though I might also look into taxr.ai based on the positive reviews here - especially if it can catch errors and handle the submission process smoothly. For anyone else still waiting, it's good to know we're not alone in this frustration. The IRS really seems to be running behind schedule this year on multiple forms. At least we have until July 31st to get everything filed, so there's still plenty of time even with the delays. Thanks everyone for sharing your experiences and solutions!

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!