One strategy I've used to manage AMT with ISOs is exercising small batches strategically throughout the year rather than doing them all at once. This helps avoid crossing into higher AMT brackets. Also, don't forget about the 83(b) election for early exercise if your company allows it! If you can exercise when the spread between strike price and FMV is small or zero, you can potentially avoid AMT altogether.

Great point about the 83(b) election, Dylan! That's definitely a strategy more people should know about. For OP's current situation though, since they've already exercised, the key decision is really about timing the sale. One thing I haven't seen mentioned yet is the wash sale rules. If you're planning to sell and potentially buy back in later, make sure you wait at least 31 days before repurchasing to avoid having the loss disallowed if the stock drops. Also, given your numbers ($33/share spread on 1,500 shares = $49,500 AMT adjustment), you're definitely in territory where professional tax advice would pay for itself. The AMT exemption phases out at higher income levels, so depending on your other income, you might be hit harder than you think. If you absolutely need the cash now, selling early might be the right move to avoid the AMT uncertainty. The difference between ordinary income rates and long-term capital gains probably won't be as painful as getting stuck with a big AMT bill you can't immediately use the credit for.

Just to add another perspective - I asked my tax accountant about a similar situation with tech stocks (selling Microsoft at a loss and buying Google), and she said it's completely fine. The key is that they're different companies with different business models, revenue streams, etc., even if they're in the same sector. She also mentioned that the IRS has never issued super clear guidance on what exactly "substantially identical" means beyond the obvious cases (like selling and buying back the same stock), so they generally interpret it narrowly.

This is a great question and you're smart to think about the wash sale implications before making the trade. Based on everything I've read and my own experience with tax-loss harvesting, you should be completely fine switching from Barrick Gold to Newmont. The IRS defines "substantially identical" very narrowly - it really only applies to the exact same security or something directly tied to it (like call options on the same stock). Two different companies, even in the same industry with similar business models, are considered distinct securities with their own unique risk profiles, management teams, asset bases, and financial structures. I've done similar sector switches myself - sold some underperforming bank stocks and bought different banks, energy companies for other energy companies, etc. Never had any issues with wash sale disallowances. The key is that GOLD and NEM are completely separate publicly traded companies with different ticker symbols, different management, different mining operations, and different financial performance. Just make sure you're making the investment decision based on your analysis of the companies' fundamentals rather than purely for tax reasons. If you genuinely believe Newmont is a better investment than Barrick going forward, then the tax loss harvesting is just a nice bonus on top of what should be a sound investment decision.

This is exactly the kind of confusion that trips up so many people! Based on everything you've described, it sounds like your employer is providing what's essentially a taxable health stipend but calling it an "HRA" - which is causing all the confusion. The fact that it's showing up in your regular paycheck and included in your W-2 taxable income is the dead giveaway. A legitimate HRA would be administered separately from payroll, require you to submit receipts for reimbursement, and wouldn't appear as taxable income on your W-2. Since you're remote and their regular plan doesn't work for your location, what they're doing makes sense from a practical standpoint - they're trying to help you out. But from a tax perspective, they've structured it as additional compensation rather than a qualified health benefit. I'd suggest having a conversation with HR to clarify whether they intended this to be a formal HRA (in which case they need to restructure it) or if they're comfortable with it being taxable supplemental pay to help with your healthcare costs. Either approach is fine, but the tax treatment should match the actual structure. Don't feel bad about being confused - the terminology around health benefits is genuinely confusing, and many employers use these terms loosely without understanding the specific legal requirements behind them.

Great question and you're definitely not an idiot! This is one of the most misunderstood areas of employee benefits. What you're describing sounds like a taxable health stipend rather than a true HRA. The key red flags are: - Money comes through regular payroll - Shows up as taxable income on your W-2 - No requirement to submit receipts or documentation A compliant HRA requires your employer to establish a formal written plan document, have you submit qualified medical expense receipts, and reimburse you outside of payroll (with no W-2 inclusion). Many well-intentioned employers call their health stipends "HRAs" without realizing there are strict IRS requirements. Your employer is trying to help, but they've structured it as taxable compensation. I'd recommend asking HR for: 1. The formal HRA plan document 2. Claims submission procedures 3. Confirmation of how reimbursements are processed If they can't provide these, then you'll know it's actually taxable income (which is fine, just different from what they're calling it). You might want to suggest they either properly structure an HRA or simply call it what it is - a health insurance stipend to help with your remote work situation.

Are we sure about the Roth IRA part? I thought kids could only contribute to retirement accounts if they're at least 18?

This is such a great opportunity for your daughter! I started hiring my 15-year-old son in my consulting business last year and it's been amazing for teaching him work ethic and financial responsibility. One thing I'd add to the excellent advice already given - consider having your daughter open that Roth IRA as soon as she starts earning. Even if she only contributes $500-1000 the first year, starting at 12 gives her decades of tax-free compound growth. The math is incredible when you start that young. Also, don't forget about state taxes. While the federal standard deduction protects most of her earnings, some states have lower thresholds or don't follow the federal standard deduction rules. Worth checking your state's specific requirements. The documentation piece that others mentioned is crucial. I learned this the hard way when I got some questions from the IRS (not an audit, just clarification). Having detailed records of what work my son actually performed and when he worked made all the difference. Good luck with this - you're giving her an incredible head start!

One thing nobody's mentioned yet - make sure you properly account for Section 197 intangibles in your sister's purchase! A big portion of that $95k likely isn't for physical assets at all, but for business goodwill, customer lists, etc. When I bought my accounting practice, the physical assets (computers, furniture, etc.) were only worth about $15k, but I paid $120k for the business. The rest was Section 197 intangibles that get amortized (not depreciated) over 15 years straight-line with no exceptions.

Great question and you've already gotten some excellent advice here! I went through something very similar when I helped my cousin set up his auto detailing business after purchasing it from someone with zero records. One additional tip that saved us headaches later: when you're allocating that $95k purchase price, be conservative with your physical asset valuations. The IRS tends to scrutinize situations where too much of the purchase price gets allocated to depreciable assets versus Section 197 intangibles (goodwill). For the pedicure chairs specifically, since you know they're from 2021, check if they qualify for any bonus depreciation. Depending on when your sister's tax year ends, she might be able to take advantage of current bonus depreciation rules for some of the equipment. Also, make sure to document everything - your research process, sources for fair market values, reasoning for your allocations. I kept a simple spreadsheet showing how I determined each value, and my accountant said it was exactly what would be needed if questions ever came up. The key is showing you used a reasonable, consistent methodology rather than just random guesses.