Everybody in the comments is just guessing based on their own experience. If you want to know FOR SURE, use taxr.ai - it's WAY more accurate than Reddit guesses. It reads your transcript and tells you exactly what's happening and when you'll get paid. I checked my transcript for weeks trying to figure it out myself before finding this tool.

Based on my experience with Chase, your refund will most likely hit sometime between 2-6 AM on the date shown on your transcript, but it could honestly come anytime during that day or even the next business day. The IRS sends the payment on the transcript date, but Chase processes it on their own schedule. I'd recommend setting up a deposit alert like someone else mentioned - way better than refreshing your account every hour! Also don't panic if it doesn't show up exactly at midnight, that's totally normal.

Don't overlook state tax implications in your planning! I noticed you mentioned your second W2 is from another state. If you're forming an LLC, you'll need to consider: 1. Which state to form it in 2. Whether you'll need to register as a foreign entity in other states 3. Whether you'll have nexus (tax presence) in multiple states 4. How your home state treats pass-through entity income I formed my consulting LLC in Wyoming for liability protection but ended up having to register in my home state too and file multiple state returns. The compliance costs eat into the tax savings. Also, if you go with option 2 and create a holding company with two LLCs, that's adding even more complexity and potential state filing requirements. Just something to factor into your decision!

I'm in a similar situation as a healthcare professional who made the transition from W2 to S-Corp last year. A few things I learned that might help: Timing is crucial - don't rush the decision while your primary employer is potentially selling. That uncertainty could work in your favor for negotiations with either the current owner or new buyers. You might get better terms (higher pay, equity stake, etc.) that could make the W2 route more attractive. For the LLC structure, I'd recommend starting simple with just one entity initially. You can always add complexity later, but managing multiple LLCs from day one creates unnecessary overhead and costs. Focus on getting one profitable before expanding. Also consider the cash flow implications - W2 gives you steady paychecks, but business income can be unpredictable, especially in the early stages. Make sure you have 6-12 months of expenses saved before making any major transitions. The tax savings are real, but they only matter if you're actually profitable. I'd suggest keeping your primary W2 job (even if terms change with new ownership) while building your LLC on the side. Once it's generating consistent income, then you can make the switch with confidence. Have you run the numbers on what your LLC would need to generate monthly to replace your W2 income after accounting for benefits, taxes, and business expenses?

One thing to remember as a tutor - you'll need to pay quarterly estimated taxes if you expect to owe more than $1,000 in taxes for the year. I learned that the hard way and got hit with an underpayment penalty my first year tutoring!

Does anyone know if we can deduct things like online tutoring subscriptions? I pay for premium Zoom and some online whiteboard tools specifically for my tutoring.

Has anyone dealt with the situation where your insolvency status changed between cancellations? My first two cancellations I was definitely insolvent, but by the third one, I had received an inheritance that pushed me into being solvent. So confused about how to report this on my taxes.

This is really helpful information! I'm in a similar situation but with only two debt cancellations coming up. One thing I'm wondering about - when calculating assets for the insolvency worksheet, how detailed do I need to be with household items? I know Owen mentioned furniture and electronics typically have minimal value, but should I actually go through and estimate values for my TV, couch, kitchen appliances, etc.? Or is it acceptable to use a reasonable estimate for all household goods combined? Also, for anyone who's been through an IRS audit on insolvency calculations - what kind of documentation did they ask for to support your asset valuations? I want to make sure I'm keeping the right records from the start.

Does anyone know if a 1098-C form impacts your ability to claim the standard deduction for your state taxes if state and federal filing statuses have to match? I'm in California and always confused about how federal choices affect my state return.

Just wanted to add my experience since I was in almost exactly the same situation last year! I donated a 2015 Honda Civic that was worth about $3,000 and got a 1098-C form. I was also unsure about itemizing vs standard deduction. The key thing I learned is that there's absolutely zero downside to accepting the 1098-C form. I ended up taking the standard deduction because my total itemized deductions were only about $11,500 (well below the $13,850 standard). The 1098-C just sits in my tax files and doesn't affect anything. One tip though - make sure you keep good records of how you determined the car's value (like KBB screenshots, recent repair estimates, etc.) just in case. Even if you don't use the deduction this year, having proper documentation could be helpful if your situation changes or if you ever need to reference the donation for other purposes. The charity should handle all the reporting requirements on their end, so you really don't need to worry about any complications from accepting the form!