Wouldn't that be considered a step transaction by the IRS though? From what I understand they look at the substance of transactions rather than just the form.

That's a valid concern about step transactions. The IRS can indeed look at the substance over form if they believe transactions were structured solely to avoid taxes. The key difference in what I suggested is that there would be a genuine business purpose - securing a specific needed asset that might not be available later. A properly structured lease with market terms that transfers actual usage rights to another party temporarily could potentially work. But you're right that it would need to be a legitimate arrangement and not just paperwork to achieve a tax outcome.

This is the correct answer right here - I don't know why no one else mentioned it! Section 179 deductions that exceed your business income can be carried forward indefinitely. So if your 2023 business income is too low to fully use the deduction, you can use the remaining amount in 2024.

Will the SSA site show my current year W-2 info though? I thought it only updates annually and wouldn't have my 2024 information available yet for filing in 2025?

You're right to question this - the SSA website typically doesn't show current tax year information in time for filing. It usually updates around July for the previous year's wages. So while it's a good resource for verifying past years or checking if old employers reported your wages correctly, it won't help with your current filing situation. For current year W-2s that you're missing, you'll need to contact either the employer directly or the IRS as others have suggested. The IRS typically has the current year information in their system before it appears in the SSA database.

Did they charge you any penalties or just the tax and interest? I'm in a similar situation but it's been 2 years and I haven't heard anything...

How long have you been using OnPay? Any issues with tax filing deadlines or deposits? We used a cheap service last year and they missed a quarterly filing which cost us penalties.

We've been on OnPay for about 3 years now. Haven't had a single issue with tax filings or deposits. Everything happens automatically and on time. The one time we had a question about a state unemployment rate change, their support team actually picked up the phone when we called - which seems rare these days. I think most payroll headaches come from the ultra-budget options that make you handle the tax filings yourself. Definitely worth paying a bit more to have that handled automatically.

I tried my bank's payroll service (won't name which one) and found it MUCH more expensive than standalone options. They charged me $75/month plus $8 per check for basically the same service as Square or Gusto.

I didn't know about this! Is it too late to use VITA if I already filed once? My income definitely qualifies.

It's definitely not too late! VITA volunteers can help with amended returns too. Just bring a copy of your originally filed return, the rejection notice, and all your tax documents (W-2s, 1099s, etc.) to your appointment. Many VITA sites operate through tax season and even a bit beyond (usually until April 15th, but some go through the October extension deadline). Call before going to make sure they're still open and to schedule an appointment, as many sites get booked up quickly.

This is really important! I once got an email saying I needed to "refile" but it was literally just one box I needed to check about healthcare coverage. Took 2 minutes to fix and resubmit on the same site.

Would the proposal likely include retirement accounts or just taxable investments? I'm nowhere near the wealth threshold, but just curious how comprehensive it would be.

Retirement accounts would almost certainly be excluded from any unrealized gains tax proposal. These accounts already have specific tax treatment - traditional accounts are tax-deferred until withdrawal, while Roth accounts are already post-tax money growing tax-free. The proposals being discussed are primarily targeting accumulated wealth in taxable accounts that currently allows some ultra-wealthy individuals to avoid income taxation by holding appreciating assets indefinitely, borrowing against them for living expenses, and never triggering taxable events through sales.

That's way too simplistic. The IRS absolutely challenges valuations on items worth significant amounts. Try valuing a $1M painting at $2M for a charitable donation and see how that goes. With billions in tax revenue at stake, they'd implement strict appraisal requirements.