One additional consideration for your house down payment timeline - you might want to think about how much you'll actually need for the down payment and closing costs. If the $4,000 represents a significant portion of your planned down payment, you definitely want to keep it safe in that HYSA. However, if this is just a smaller piece of a larger down payment fund, you could potentially be a bit more strategic. For example, you could keep the amount you absolutely need in the HYSA and put any "extra" into slightly higher-yield options like CDs or Treasury securities that mature closer to your purchase date. Also worth mentioning - some mortgage programs have down payment assistance or allow for lower down payments than the traditional 20%. Depending on your situation, you might not need as large a down payment as you think, which could give you more flexibility with how you invest this money. Just make sure to factor in PMI costs if you go with less than 20% down. The tax withholding decision you're making is definitely the right call given your situation!

Great discussion here! One thing I'd add regarding the tax withholding decision - since you know you have $1,200 in taxable gains, you might also want to consider your overall tax situation for the year. If you typically get a refund, having them withhold the 10% ($120 on the taxable portion) might result in a slightly larger refund. But if you usually owe money at tax time, this withholding could help reduce what you owe. Also, regarding the investment timeline - I'm seeing some people mention I Bonds, and while they're great for inflation protection, keep in mind you lose 3 months of interest if you cash them out before 5 years. Given your 2027-2028 timeline, you'd likely be cashing out between 3-4 years, so you'd forfeit some interest. Still might be worth it for the inflation protection on a portion of your funds, but factor that into your calculations. Your HYSA strategy is really the most prudent approach here. House down payments are one of those financial goals where preservation of capital trumps growth potential every time.

I just went through this last year. The most important thing is timing - if the annuity company already cut the check to the estate with 20% withholding, unfortunately you've likely lost the ability to do any kind of inherited IRA rollover. The distribution to the estate is considered the taxable event. Remember that on the 1041, you'll report the FULL amount of the annuity as income (including the 20% withheld), and then show the withholding as a credit. When the estate distributes the money to you, you'll receive a K-1 showing your share of the estate's income, deductions, etc. One potential silver lining - check if the deceased had any unrecovered investment in the annuity contract. If they made after-tax contributions to the annuity, a portion of the distribution might be non-taxable return of basis.

I'm dealing with a very similar situation right now with my aunt's estate. One thing that might be worth exploring - and I'm not sure if this applies to your specific case - is whether the annuity company properly followed the required distribution procedures when there's no named beneficiary. In some cases, if the annuity company didn't give proper notice to potential beneficiaries or follow state law requirements for estate distributions, there might be grounds to challenge the distribution method. I've heard of situations where this led to the ability to "undo" the estate distribution and have it paid directly to the heir instead. You might want to review the annuity contract terms and your state's laws about how these distributions should be handled. If there were procedural errors, it could potentially open up options that wouldn't normally be available once the money hits the estate. Also, make sure you're not missing any deadlines for estate tax elections or other time-sensitive decisions. Some states have different rules about inherited annuities that could affect your tax situation.

I'm in a similar boat with multiple jobs and my tax situation got so confusing last year. Does anyone know if TurboTax handles multiple W-2s well? Or should I pay for an actual accountant this time?

Great question! I was in a similar situation a few years ago and learned some hard lessons. With your combined income of around $63,000, you'll definitely want to be proactive about withholding. One thing to keep in mind is that restaurant work often involves tips, which are taxable income that may not have proper withholding. If you're serving tables, make sure to track all your tip income carefully and consider that when calculating your total annual earnings. The "different tax bracket" comment from your manager is referring to how your marginal tax rate increases as your income goes up. While you won't pay the higher rate on all your income (that's a common misconception), the additional $15K will likely be taxed at 22% instead of the 12% rate that covers most of your main job income. My recommendation: Use the IRS withholding calculator online to get specific guidance for your situation, or consider having extra tax withheld from your main job's paycheck. I'd rather get a refund than owe money when saving for a house down payment! Also, keep good records of any work-related expenses from the restaurant job.

Have you looked into retirement accounts as a tax strategy? Maxing out 401ks, HSAs, and potentially setting up a SEP IRA or Solo 401k for any self-employment income would reduce your taxable income significantly. This approach is usually more straightforward and definitely beneficial compared to forming business entities that might not actually save you anything on W-2 income.

As a travel healthcare worker myself, I can relate to your situation! One thing I'd add that hasn't been fully covered - make sure you're maximizing ALL your legitimate business deductions for your social media/Instagram activities if you do decide to monetize it. Even without forming an LLC, if you're earning income from your Instagram (sponsorships, affiliate marketing, etc.), you can deduct expenses like your phone/internet costs (business portion), camera equipment, editing software, travel expenses when creating content, etc. These deductions reduce your taxable income dollar-for-dollar. I'd recommend starting there before worrying about business structures. Track your social media income and expenses for a few months to see if it's actually profitable enough to justify the complexity of an LLC or S-Corp. Many people jump into business formations without realizing their side hustle isn't even making enough to cover the additional costs and paperwork. Also, definitely consult with a tax professional who understands healthcare travelers - the stipend/tax home issues mentioned above are crucial and commonly misunderstood!

Has anyone considered that they might be treating the holding period differently? I noticed that GainsKeeper and TradeLog sometimes differ in how they treat the holding period after a wash sale adjustment. GainsKeeper tends to restart the holding period for the entire position after a wash sale, which is generally correct per IRS rules. But TradeLog sometimes maintains separate lots with different holding periods which can affect how they allocate the adjustments across different lines on Form 8949. This becomes really important if you're straddling the line between short-term and long-term capital gains. Might explain why they're treating lines 4 and 5 differently if those involve positions with complicated holding period calculations.

Great to hear you figured it out! The $43 difference across 220+ trades is actually pretty impressive accuracy for both systems. That small variance is likely just rounding differences in how they handle fractional shares or timing calculations. You made the right choice going with GainsKeeper since it aligns with your 1099-B format. This is exactly why I always recommend starting with whatever matches your brokerage reporting - it makes everything so much cleaner if you ever get questioned by the IRS. For anyone else dealing with similar wash sale software discrepancies, Natasha's approach here is spot on: compare the bottom line totals first, then choose the method that best matches your actual brokerage statements. The IRS cares much more about the final numbers being economically accurate than the specific methodology used to get there. One last tip - keep both reports in your tax files even though you're only using one. If you ever get audited, having the alternative calculation that produced nearly identical results actually strengthens your position by showing you did your due diligence.