This is such a common situation unfortunately! I went through something similar last year and learned the hard way that the IRS has very specific criteria for determining employee vs contractor status. The key factors are behavioral control (do they control HOW you work?), financial control (do they control the business aspects of your work?), and the type of relationship. Working in their office on a set schedule with their equipment strongly suggests you should be classified as a W-2 employee. The fact that they didn't mention this during interviews is concerning - legitimate contractor relationships are usually discussed upfront since they're fundamentally different from employment. At $27/hour for 20-30 hours weekly, you're looking at roughly $1,100-$3,500 in additional self-employment taxes annually compared to W-2 status. Plus you'll need to make quarterly estimated payments and handle your own benefits. I'd recommend having a direct conversation with them about proper classification before accepting. Most legitimate employers will appreciate you bringing this up professionally rather than discovering compliance issues later. If they refuse to consider W-2 status, that tells you something important about how they operate. Good luck with whatever you decide - trust your instincts on this one!

This is exactly why I always research employment classification before accepting any position! The IRS has a really helpful publication (Publication 15-A) that outlines the specific criteria for determining worker classification. One thing that hasn't been mentioned yet - if you do end up taking a contractor position, make sure you get everything in writing. A proper independent contractor agreement should specify deliverables, deadlines, and payment terms rather than hourly schedules and office requirements. Also, keep detailed records of everything work-related if you go the W-9 route. While commuting isn't deductible, you might be able to deduct things like a portion of your phone bill, office supplies you purchase, or professional development costs depending on the nature of the work. But honestly, based on what you've described (in-office work, set hours, their equipment), this really sounds like an employee relationship. The fact that multiple people here have successfully gotten reclassified suggests it's worth having that conversation. Don't let them take advantage of you just because you need the job!

I'm new to this community but had to jump in because my partner and I are dealing with this exact same situation! We just moved in together after graduation and have been doing identical money transfers - splitting rent, groceries, utilities, and contributing to our shared emergency fund. Reading through this entire thread has been such a relief! I was honestly getting really anxious about whether our constant Venmo and bank transfers were going to create some kind of tax nightmare when we file next year. The consistent message from everyone here - especially the tax professionals who commented - is so reassuring. What really helps is seeing how many people have been through this exact worry and can confirm that routine expense sharing between partners is completely normal from a tax perspective. The IRS expects couples to share living expenses regardless of whether they're married or not. I love the practical tips people shared about keeping simple notes on transfers and basic record keeping. It seems like the key is just being able to show these are legitimate shared expenses, though apparently even that's rarely necessary. Thanks to everyone who contributed to this discussion - this thread should definitely be bookmarked for other young couples navigating shared finances for the first time!

As someone who was in this exact situation just two years ago, I completely understand your anxiety! My partner and I were doing the same thing - constantly transferring money for rent, groceries, utilities, and building our joint emergency fund. I was convinced we were going to accidentally trigger some kind of IRS investigation. After going through our first tax season together and doing extensive research, I can confirm what everyone else here is saying: you're absolutely fine. Regular expense sharing between romantic partners is completely normal and expected by the IRS, regardless of marital status. What really helped me stop worrying was realizing that millions of couples across the country do exactly what you're doing every single day. You're not doing anything unusual or complicated - just standard relationship financial management. The joint savings account approach you mentioned is actually really smart financial planning. Keep building that emergency fund and saving for your vacation goals - you're clearly being responsible about money management as a couple. One small tip that gave me peace of mind: I started adding brief descriptions to our larger transfers (like "monthly rent split" or "grocery reimbursement"). It's not required, but it helps create a clear record of what everything was for. Focus on your financial goals together rather than stressing about routine transfers. You're doing everything right!

Make sure you keep REALLY good records of this sale and your basis calculation for at least 7 years. My dad got audited 3 years after selling inherited property because the IRS assumed his basis was $0 since he couldn't immediately produce documentation of the stepped-up value. It was a nightmare getting it all sorted out.

This is a really common situation that trips up a lot of people! The fact that you received a 1099-S doesn't automatically mean you owe a lot in taxes - it's just the IRS's way of tracking the transaction. Since you inherited the property, you likely benefit from what's called a "stepped-up basis" which means your tax basis is the fair market value when your grandmother passed away 3 years ago, not what she originally paid for it. If the property was worth close to $5,800 back then, you might owe very little or even nothing. To figure out your actual tax liability, you'll need to determine what the property was worth when you inherited it. Check the county tax assessor's records for the assessed value around that time, or look for comparable sales data from 3 years ago. The difference between that value and your $5,800 sale price is what you'd potentially owe capital gains tax on. As for quarterly payments, you only need to worry about that if the gain would result in owing $1,000+ in additional tax AND your regular withholding from other income won't cover 90% of this year's total tax liability. Given the small sale amount and likely stepped-up basis, this probably won't be an issue for you. Don't panic - inherited property sales are usually much more tax-friendly than people expect!

Quick tip if you filed your federal taxes for those years - go to the Ohio Department of Taxation website and look at your state tax transcripts. Since RITA is for Ohio municipalities, your state returns might have the info they need to verify your local tax obligations.

Have you tried contacting your former employer's payroll company directly? Even when a business shuts down, their payroll service (like ADP, Paychex, etc.) often retains records for several years. If you can remember who handled payroll or find it on an old pay stub, they might be able to provide duplicate W2s much faster than going through the IRS. Also, check if your state has an unclaimed property database - sometimes when companies dissolve, final paychecks and tax documents end up there. It's a long shot but worth a quick search since you're pressed for time. For the immediate RITA situation, definitely call them today and explain that you're actively working to obtain the documents from a defunct employer. Most tax authorities will work with you if you show good faith effort, especially when the delay isn't your fault.

I actually made the same mistake in 2021 and found out through a tax notice. Here's what I learned: Your W-2s from both employers should show your total contributions in Box 12 with code D (traditional) or AA (Roth). Add those up to confirm you actually exceeded the $20,500 limit for 2022. If you did exceed it, and it's a Roth 401k, the excess plus earnings should be distributed to you. The earnings will be taxable in 2023 (when you receive the distribution), not 2022. But theres a 10% early withdrawal penalty on those earnings if you're under 59½.

Just wanted to add some perspective from someone who dealt with this exact situation last year. The stress is real, but you're not alone in this! A few practical tips that helped me: 1. **Document everything** - Keep records of all your communication attempts with Vanguard and your employer. This creates a paper trail showing you made good faith efforts to resolve it properly. 2. **Check your math twice** - Like Isabella mentioned, make sure you're looking at the right W-2 boxes. I initially panicked thinking I was over when I was actually fine. 3. **Don't panic about the October 15 deadline** - While it's ideal to get the excess distributed before then, you can still file Form 5329 with your return to report the excess and pay the 6% excise tax if needed. It's not the end of the world. 4. **Consider professional help** - Whether it's the services others mentioned or a local CPA, sometimes the cost is worth the peace of mind and avoiding bigger penalties. The key thing to remember is that this is a correctable mistake. The IRS has procedures for this exact situation because it happens more often than you'd think with job changes. You're taking the right steps by addressing it now rather than ignoring it. Hang in there - you'll get through this!