Don't forget to consider state taxes too! Federal estate taxes might not apply if the estate is under the exemption amount (currently over $12 million), but some states have much lower thresholds. I learned this the hard way with my mother's estate in Oregon, which has a $1 million exemption. We focused so much on the federal aspects that we missed significant state tax implications. Might be worth checking your state's rules.

Connor, I'm sorry for your loss. You're absolutely right to be concerned about the estate income tax implications - this is a common trap that catches many people off guard. The key insight you've discovered is correct: distributing the IRA and brokerage assets to the heirs within 2024 can indeed help you avoid the compressed estate income tax brackets (which top out at 37% on income over $15,200 for 2024). When you distribute these assets, the income gets "passed through" to the beneficiaries and is taxed at their individual rates instead. A few critical points to consider: 1. **Timing is everything** - The distributions need to actually happen in 2024, not just be authorized. This means completing all the paperwork and transfers before December 31st. 2. **Documentation matters** - Make sure you're properly tracking the "income in respect of a decedent" (IRD) amounts. The beneficiaries will need this information for their personal tax returns. 3. **Consider a partial strategy** - You don't have to distribute everything at once. You could do a partial distribution this year to reduce the estate's income, then continue distributions in 2025 based on what works best for each heir's tax situation. I'd strongly recommend getting both an estate attorney and a tax professional involved before making these distributions. The potential savings are significant, but you want to make sure you're executing this properly to avoid any complications down the road.

For married couples, you almost always come out ahead filing jointly rather than separately. Filing separately comes with a lot of limitations and usually results in paying more tax overall. In 2023, if filing separately, each spouse gets a standard deduction of $13,850 (not the full $27,700 joint amount). Plus, if one spouse itemizes, the other MUST itemize too - even if that results in a higher tax bill. You lose a bunch of tax benefits when filing separately too.

Great point about the student loan repayment plans! There are definitely exceptions to the "married filing jointly is always better" rule. Income-driven repayment plans, potential eligibility for certain tax credits, and situations involving significant medical expenses or casualty losses can sometimes make married filing separately worthwhile. For the original poster though, with only $15,000 in business income and likely no major itemized deductions, married filing jointly would probably be the way to go. You'd get the full $25,900 standard deduction (or $27,700 for 2023) which would eliminate your income tax liability entirely. Just make sure to factor in that self-employment tax that Ashley mentioned - that's going to be your main tax burden here, not income tax.

Just to clarify something important: the IRS doesn't actively "investigate" couples to determine if they're married unless there's a red flag or audit trigger. They generally accept whatever filing status you claim. BUT - they can and do compare addresses across returns. With your high incomes, if you're living together and filing as single, that could trigger questions. To minimize risk: - Don't claim the same housing-related deductions on both returns - Be consistent with how you title property and financial accounts - Don't refer to each other as spouses on any official documents - If you have joint accounts, make sure the interest/dividends are allocated proportionally I've been a preparer for 15 years and seen this situation often. Most clients in your position decide the legal protections of marriage outweigh the tax penalty, but for those who don't, just be consistent and document your intentions.

I went through this exact same situation two years ago with similar income levels. We ended up doing the religious ceremony without the legal marriage and have successfully filed as single for two tax seasons now. A few practical tips from our experience: 1. Keep excellent documentation of your decision - we have a written record of why we chose not to get a marriage license, which our tax attorney said was smart in case of questions later. 2. Be very careful about beneficiary designations on retirement accounts. We learned that some 401(k) plans require spousal consent for non-spouse beneficiaries, but since we're not legally married, this doesn't apply. However, we had to be explicit with HR that we're unmarried to avoid confusion. 3. Consider the timing if you ever do decide to legally marry later. Getting married on January 1st vs December 31st can make a huge difference in your tax liability for that year. 4. We found that having separate tax preparers actually helped - it avoids any appearance that we're coordinating our returns inappropriately, even though we're doing nothing wrong. The religious ceremony was beautiful and meaningful to us, and we've saved over $15,000 in taxes over two years. For our situation, it was absolutely the right choice.

As a newcomer to this community, I just wanted to say thank you for such an informative and helpful discussion! I'm currently dealing with a nearly identical situation - I was laid off from my job in January and just started a new position this month, and I've been completely confused about how to handle the W4 form. Reading through everyone's responses has cleared up so much confusion for me. The key insight that the "multiple jobs" section is for concurrent employment rather than sequential jobs throughout the year makes perfect sense now that it's been explained. I was definitely overthinking this and worried I might mess up my withholding. What really stands out to me is how many people have mentioned the IRS Tax Withholding Estimator as the go-to tool for these situations. I had no idea this free resource existed! It sounds like the most accurate way to determine if any additional withholding is needed based on combined income from different jobs throughout the year. I'm feeling much more confident now about filling out my W4 - keep it simple, focus on current employment status, and use official IRS tools when in doubt. This community is such a valuable resource for navigating these tricky tax situations!

As someone new to this community, I wanted to add my perspective since I went through this exact situation last year! I switched jobs in April after being unemployed for two months, and I was just as confused about the W4 form. Everyone here has given excellent advice - the "multiple jobs" checkbox is definitely only for when you're working multiple jobs simultaneously, not for different jobs you've had throughout the year. Since you're only working at Company B right now, you absolutely should not check that box. What I found most helpful was using the IRS Tax Withholding Estimator that several people have mentioned. I was able to input my income from my previous job, my expected income from my new job, and what had already been withheld. It calculated exactly how much extra I should have withheld per paycheck to avoid owing taxes at filing time. In my case, I ended up adding $40 extra per paycheck on line 4(c) of my W4, and when I filed my taxes this year, I actually got a small refund instead of owing anything. The peace of mind was totally worth it! One thing I learned is that it's always better to be slightly over-withheld than under-withheld, especially when you've had income changes throughout the year. Good luck with your new job!

Don't feel overwhelmed - you're not alone in finding ESPP taxes confusing! The key is to tackle it systematically. First, gather all your documents: Form 3922s from each purchase period, your purchase confirmations, and any 1099-B forms from sales. For each sale, you'll need to determine: 1) Was it a qualifying or non-qualifying disposition based on the holding period rules? 2) What's your correct cost basis (purchase price + any discount already taxed)? 3) What additional ordinary income needs to be reported for non-qualifying dispositions? I'd recommend creating a simple spreadsheet listing each sale with purchase date, offering date, sale date, purchase price, FMV at purchase, and sale price. This will help you see which sales are qualifying vs non-qualifying and calculate the tax treatment for each. If you're still feeling lost after organizing everything, consider consulting a tax professional who has experience with employee stock plans. The peace of mind is often worth the cost, especially when dealing with multiple years of ESPP participation.

I went through a very similar situation last year when I left my company and had ESPP shares to deal with. Here's what I learned that might help you: First, you're right that you won't get a W-2 from your former employer for the stock sales - that discount was already reported when you made the purchases while employed. You'll get a 1099-B from your brokerage instead. The tricky part is that many brokerages don't report the correct cost basis for ESPP shares on the 1099-B. They often miss the discount amount that was already taxed as ordinary income, which means you could end up paying taxes twice on that portion if you're not careful. Here's what saved me: I dug up all my old ESPP statements and Form 3922s (if your company issued them) to reconstruct the correct cost basis for each lot of shares. Your cost basis should be: what you actually paid + the discount that was reported as income on your W-2. For the sale timing, if you held the shares more than 1 year from purchase AND more than 2 years from the offering date, it's a qualifying disposition (better tax treatment). If not, you'll have additional ordinary income to report. I'd strongly recommend keeping detailed records and consider getting help from a tax professional if you have multiple purchase periods - it can get complex quickly, but it's definitely manageable with the right approach!