Quick tip: if you expect to pay freelancers regularly, consider getting an EIN instead of using your SSN for everything. It's free and you can do it online in like 10 mins. It adds a layer of legitimacy to your business and helps with identity protection since you won't be giving out your SSN.

Just wanted to add that you should also keep track of any fees Upwork charged you for using their platform - those are deductible business expenses too! I made the mistake of only tracking what I paid the freelancers and missed out on deducting the service fees. On Schedule C, the freelancer payments go on line 11 (contract labor) and the Upwork fees would typically go on line 10 (commissions and fees). Also, if you're planning to continue hiring freelancers regularly, consider setting up a separate business bank account even as a sole proprietor. It makes record-keeping so much easier come tax time and helps establish that clean separation between personal and business expenses that the IRS likes to see.

As a tax professional, I wanted to add some clarity on a few technical points that might help with your decision-making process. First, regarding the "double contribution" catch-up rule mentioned earlier - this is called the "special catch-up contribution" and it's incredibly valuable, but there's an important limitation: you can only use unused contribution room from years when you were eligible to participate in the plan. So if you just started contributing this year, you'd need to track your under-contributions going forward to use this benefit later. Second, for your specific situation at $63,500 income, you're in the sweet spot where both accounts make sense. Your effective tax rate on the 457(b) contribution is probably around 22%, which means every $1,000 you contribute saves you roughly $220 in current taxes. But with 30+ years until retirement, that same $1,000 in a Roth could grow to $10,000+ tax-free (assuming 7% annual returns). One strategy I often recommend for government employees: contribute enough to your 457(b) to bring your taxable income down to exactly $47,150 (the bottom of the 22% bracket), then put everything else into a Roth IRA up to the $7,000 limit. This maximizes your current tax savings while still building that tax-free bucket for the future. Don't forget that as a government employee, you likely have access to excellent healthcare benefits in retirement too, which reduces the pressure on your retirement accounts to cover those costs. This makes the tax diversification between 457(b) and Roth even more valuable since you'll have more flexibility in managing your retirement income.

The advice in this thread has been phenomenal! I'm also a government employee (federal rather than county) and went through this exact same decision process about two years ago. What really helped me was creating a simple spreadsheet to track the tax impact of different contribution scenarios. One thing I'd add that might be helpful for @Serene Snow - don't overlook the administrative simplicity factor. Your 457(b) contributions come straight out of your paycheck automatically, which makes it super easy to stick with. For the Roth IRA, you'll need to set up your own account (Vanguard, Fidelity, Schwab are all good options) and either automate contributions from your bank account or remember to contribute manually. I started with the "set it and forget it" approach - kept my 457(b) at 6% of salary for the convenience, then set up automatic monthly transfers of $300 to a Roth IRA. The automation was key because it removed the temptation to skip months or reduce contributions when other expenses came up. Also, since you mentioned being confused about retirement accounts generally, I'd recommend checking if your county offers any financial wellness seminars or retirement planning resources through HR. Many government employers provide free access to financial advisors or educational workshops that can help you understand your specific benefits package better. Sometimes having someone walk you through your actual plan documents makes everything click much better than trying to figure it out from general online advice. The fact that you're asking these questions at 32 puts you in great shape - you have plenty of time to course-correct if needed!

As a newcomer to this community, I just wanted to say how helpful this entire thread has been! I'm also filing taxes for the first time this year and had the exact same confusion about what to do with my W-2 after e-filing. Reading through everyone's responses has been incredibly reassuring. It's clear that e-filing really is as straightforward as it seems - no additional mailing required! I love the practical tips about document organization too. I'm definitely going to set up that simple filing system with a folder for this tax year. It's so nice to see a community where people take the time to help first-time filers without making us feel stupid for asking basic questions. The tax process can be really intimidating when you're doing it on your own for the first time, but threads like this make it so much more manageable. Thanks to everyone who shared their knowledge and experience!

As another newcomer to this community and first-time tax filer, I can't thank everyone enough for this incredibly helpful discussion! I was literally about to drive to the post office to mail my W-2 after e-filing because I was so confused by conflicting information I found online. Reading through all these responses has been such a relief - it's clear that e-filing really does mean you're completely done with the submission process. No stapling, no mailing, no additional steps required! I love how everyone has shared both the technical answer and their personal experiences. It makes me feel so much less alone in navigating this process. The document organization advice is gold too. I'm definitely going to create that simple filing system right now while it's fresh in my mind. It's such a small step but will probably save me so much stress down the road. This thread perfectly demonstrates why community forums are so valuable - getting real answers from real people who've been through the same confusion. Thank you all for taking the time to help us newbies figure this out!

I just want to point out that intentionally breaking up deposits to avoid reporting requirements (called "structuring") is actually illegal, even if the money is 100% legitimate. I've seen people mention this but want to emphasize it - depositing the full $4k at once is actually LESS suspicious than doing 4 separate $1k deposits.

I'm sorry for your loss. As others have mentioned, $4,000 is well below the $10,000 threshold for mandatory bank reporting to the IRS, so you should be fine depositing it all at once. One thing I'd add that might help ease your mind - keep a simple written record of what this money was for. Something like "Cash inheritance from Uncle [Name] - designated for funeral expenses, deposited [date] to pay credit card used for funeral costs." This isn't required for the bank, but it's good practice for your own records in case you ever need to reference it later. Also, while this cash won't trigger any IRS reporting, remember that inheritance itself generally isn't taxable income to you as the recipient - it's the estate that would handle any tax obligations. So even from a tax perspective, you're in the clear. Take care of yourself during this difficult time.

@Aaron Lee (the original poster) - I wanted to circle back to your specific situation since there's been so much great advice in this thread! Based on what you described (8 bags of clothing donations plus cash donations throughout the year), here's what I'd recommend: First, contact the shelter where you donated the clothes ASAP to get a receipt if you don't have one already. Most shelters are used to providing these retroactively. For valuing those 8 bags, use the "thrift store test" others mentioned - think about what each category of items would actually sell for at a thrift store, not what you originally paid. Since you file MFJ, your 2025 standard deduction will likely be around $29,200. To benefit from itemizing, your total deductions (charitable donations PLUS mortgage interest, state/local taxes, medical expenses, etc.) need to exceed that amount. Don't just look at donations in isolation. Given the volume of your donations, it might actually be worth paying for a consultation with a tax professional this year, especially since you mentioned never tracking donations before. They can help you properly value everything and determine if itemizing makes sense. You could also try some of the tools mentioned in this thread like taxr.ai to get a better sense of your total deductible amounts. The key is getting organized now while the donation is still fresh in your memory, rather than scrambling at tax time!

One important thing I haven't seen mentioned yet is that for clothing donations valued over $500, you'll need to file Form 8283 (Noncash Charitable Contributions) with your tax return. This form requires more detailed information about each item donated, including the date acquired, how you acquired it, and your cost basis. Also, if any single clothing item is valued at more than $5,000 (like a designer dress or expensive coat), you'll need a qualified appraisal. Most regular clothing donations won't hit this threshold, but it's worth keeping in mind if you donated any high-end items. Another tip: keep a detailed list of what you donated by category. Instead of just writing "8 bags of clothes - $400," break it down like "10 men's shirts - $40, 6 pairs women's jeans - $60, 5 sweaters - $50" etc. This level of detail will be crucial if you're ever audited and shows the IRS you made a good faith effort to properly value your donations. The combination of your clothing donations plus cash contributions might actually get you closer to making itemizing worthwhile than you think, especially when you factor in your other potential deductions!