Great point about checking email for electronic W2s! I'd also suggest checking if you have any old paystubs saved - either physical copies or in your email. While paystubs aren't a direct substitute for W2s, they can help you calculate your total annual wages and withholdings if you have them for the full year. This information can be useful when requesting transcripts from the IRS or explaining your situation to lenders, as it shows you have some documentation of your employment and earnings during those years.

Just went through this exact situation last year when my employer suddenly shut down. One thing that really helped me was contacting the bankruptcy trustee if you can find out who's handling the case. They sometimes have access to HR records including W2 information, or can at least confirm employment dates which helps when dealing with the IRS. You can search for bankruptcy cases on PACER (pacer.gov) using your company name to find the trustee's contact info. Even if they can't provide the actual W2s, having official documentation of the bankruptcy can strengthen your case when requesting wage transcripts from the IRS or explaining the situation to your lender. Also, don't overlook checking with your state's Department of Labor - they sometimes maintain employment records that can serve as backup documentation of your work history and wages during those years.

Has anyone successfully used the sales tax deduction calculator in previous years? I'm wondering if it's worth the effort or if I should just stick with my state income tax deduction.

I'm in a similar boat with itemizing for the first time this year! The IRS usually updates their calculators around December/January, so it's totally normal that 2024 isn't available yet. For now, you can get a rough estimate by using last year's calculator and adjusting for any major purchases you made in 2024. Since you mentioned big purchases with your new house, don't forget that you can also deduct sales tax on things like furniture, appliances, and even your car if you bought one this year - just keep all those receipts! The key is to compare your estimated sales tax deduction against your state income tax amount when you're ready to file. Whichever is higher is what you'll want to claim. Given that you're itemizing anyway for mortgage interest, it's definitely worth running both calculations to see which gives you the bigger deduction.

Don't forget to also check if what you're selling is actually taxable in each state. For example, clothing is tax-exempt in some states but taxable in others. Digital products have their own weird rules too. The nexus threshold isn't the only thing to consider...

Great question! You're mostly correct about economic nexus thresholds - staying under $100k in sales or 200 transactions typically means you don't need to collect sales tax in most states. However, there are a few important things to keep in mind: 1. **Home state physical nexus**: You'll still need to collect sales tax for customers in your home state regardless of your sales volume, since you have physical presence there. 2. **Etsy handles most of it**: Since you're selling on Etsy, they actually collect and remit sales tax for you in most states under marketplace facilitator laws. This is a huge advantage and simplifies things significantly. 3. **Keep records**: Even though you're under the thresholds now, it's good practice to track your sales by state so you'll know when you're approaching any limits if your business grows. 4. **Product taxability**: Handmade jewelry is generally taxable, but it's worth double-checking your specific state's rules since some have exemptions for certain handcrafted items. At your expected sales volume of $2,500-3,000, you're definitely safe from economic nexus in other states. Just make sure you understand your home state's requirements for small sellers - some states have minimum thresholds or simplified processes for micro-businesses.

One additional strategy worth considering is income smoothing through installment sales if you're planning to sell a large portion of your RSUs. While this doesn't work for publicly traded stocks immediately after IPO, if you're considering selling to a private buyer or in certain structured transactions, installment treatment can spread the tax impact over multiple years. Also, don't overlook the Net Investment Income Tax (NIIT) - that additional 3.8% tax kicks in at $200K for single filers or $250K for married filing jointly. If your RSU sales combined with other income push you over these thresholds, it's another factor to consider in your timing strategy. For those with significant RSU positions, it might also be worth exploring tax-efficient index fund investing with your other assets. If you're going to be heavily concentrated in your company stock post-IPO, you can use tax-loss harvesting on a diversified portfolio to generate losses that offset some of your RSU gains. One more thing - if you're planning any major life changes (marriage, divorce, having children) around the time of your IPO, the timing of these events relative to your stock sales can have significant tax implications due to filing status and dependent changes.

Great comprehensive discussion here! I wanted to add a few additional considerations that might be helpful for your pre-IPO RSU planning: **Roth IRA Conversions**: If you expect to be in a higher tax bracket post-IPO, consider doing Roth IRA conversions now while you're in a lower bracket. You'll pay taxes on the conversion at today's rates, but future growth and withdrawals will be tax-free. This is especially powerful if you can use some of your future RSU proceeds to fund retirement. **Section 83(b) Elections**: While this typically applies to early-stage restricted stock rather than RSUs, if your company offers any opportunity to exchange RSUs for restricted stock before IPO, the 83(b) election could potentially save significant taxes by locking in today's (presumably lower) valuation for tax purposes. **Consider AMT implications**: If you have any incentive stock options (ISOs) in addition to RSUs, be careful about triggering Alternative Minimum Tax. The timing of your RSU sales relative to ISO exercises could impact your overall tax efficiency. **International tax considerations**: If you have any foreign accounts or investments, or if you're planning to move internationally, FATCA reporting requirements and foreign tax credits can add complexity to your post-IPO tax situation. The key is starting this planning now rather than waiting until after the IPO when your options become more limited. Having multiple strategies in your toolkit gives you flexibility to adapt based on the actual IPO price and market conditions.

I understand your frustration - trust taxation can be incredibly confusing, and it sounds like there may have been some miscommunication about the specific benefits your irrevocable trust provides. The general rule is that irrevocable trusts DO pay capital gains taxes when property is sold, using the same basis (original purchase price plus improvements) that you had when you transferred the property into the trust. However, there are several important nuances that might explain the confusion: 1. **Estate Tax vs. Income Tax Benefits**: Your attorney was likely correct about the estate tax advantages - irrevocable trusts remove assets from your taxable estate, which can save significant money in estate taxes for larger estates. 2. **Grantor Trust Rules**: Some irrevocable trusts are still considered "grantor trusts" for income tax purposes, which means the tax consequences flow through to you personally rather than being taxed at the trust level. 3. **Special Trust Types**: Certain specialized trusts like Charitable Remainder Trusts (CRTs) or Qualified Personal Residence Trusts (QPRTs) have different capital gains treatment. My recommendation would be to: - Review your trust documents carefully to identify the exact type of trust you have - Consult with a tax attorney or CPA who specializes in trust taxation for a second opinion - Ask specifically about any grantor trust provisions or special elections that might apply Don't despair - even if capital gains avoidance wasn't actually part of the package, your trust likely still provides valuable asset protection and estate planning benefits that may justify its existence.

Reading through all these responses has been incredibly enlightening! I'm in a similar situation where my family's estate attorney told us our irrevocable trust would help with taxes, but wasn't specific about which taxes. One thing I wanted to add that hasn't been mentioned yet - the timing of when property was transferred into the trust can also matter for tax purposes. Properties transferred into irrevocable trusts retain their original cost basis, but if the grantor dies while still being treated as the owner for income tax purposes (grantor trust rules), the property can potentially receive a stepped-up basis at death. For those asking about 1031 exchanges with trust-owned property - yes, they can work! I successfully completed a 1031 exchange last year with property held in our family's irrevocable trust. The key is making sure the trust qualifies as the "taxpayer" for the exchange and that all the strict timing requirements are met. The replacement property must also be titled in the same trust. @GalaxyGlider - I'd definitely recommend getting that second opinion from a tax professional who specializes in trusts. Don't feel bad about the confusion - this area of law is complex and even professionals sometimes give incomplete information. The important thing is understanding what you actually have now so you can make informed decisions going forward.