This is such helpful information! I had no idea about the stepped-up basis rule - that's a huge relief. So just to make sure I understand correctly: if my parents do the 1031 exchange to get the bigger property, and then later I inherit it, I basically get a "clean slate" with the property valued at whatever it's worth when they pass away, right? And then if I keep it as a rental, I can start depreciating from that new higher value? That actually sounds like it could work out really well tax-wise. I'm definitely going to share this thread with them - sounds like the 1031 exchange could be a smart move for multiple reasons beyond just deferring their current taxes. Thanks everyone for breaking this down in terms I can actually understand!

One thing to keep in mind is that while the stepped-up basis rule is incredibly beneficial, your parents should also consider the cash flow implications of the 1031 exchange. Moving from a fully depreciated property (where they're getting maximum depreciation benefits) to a new property means they'll be starting over with depreciation on the replacement property too. The new property will likely have a much higher basis for depreciation purposes, which could actually increase their annual depreciation deductions and reduce their taxable rental income during their lifetime. This could be especially valuable if they're in a high tax bracket now. Also, make sure they consider the condition and potential maintenance costs of the new property versus keeping their current fully-paid-off rental. Sometimes the devil is in the details beyond just the tax benefits!

The whole "billionaires don't pay taxes" thing is often misunderstood. They DO pay taxes - just not on unrealized gains (stock they haven't sold yet). Nobody pays taxes on unrealized gains. The real advantage they have is: 1) They can afford to never sell (living off loans using their stock as collateral) 2) They can time their sales perfectly for tax planning 3) If they hold until death, heirs get a stepped-up basis (meaning gains during their lifetime are never taxed) 4) They have access to sophisticated tax planning strategies and high-priced accountants For regular employees with RSUs or stock options, the best approach is usually a diversification strategy where you systematically sell company stock after vesting to reduce concentration risk, regardless of tax considerations.

This is such a common frustration, and you're absolutely right that the system feels unfair. I went through the same thing for years - watching a third of my RSUs disappear immediately to taxes while reading about billionaires paying zero. One thing that helped me was understanding that we can actually learn from some of the strategies the wealthy use, just on a smaller scale. After your RSUs vest and you've paid the income tax, any additional gains on the shares you keep are treated as capital gains (not ordinary income). If you can afford to hold onto some of those shares instead of selling everything immediately, you get similar tax treatment to what billionaires get on their holdings. I also started timing my stock sales more strategically - selling some in years when my income is lower, or pairing sales with capital losses from other investments to offset gains. It's not going to make you a billionaire, but these small optimizations can add up over time. The key difference is billionaires have enough wealth that they never NEED to sell, while we often have to sell to cover living expenses. But even keeping 20-30% of your vested shares (if financially feasible) can help you benefit from the same long-term capital gains treatment they use.

Also important - make sure you're tracking business use vs. personal use! If you're using that laptop 70% for business and 30% for Netflix, you can only deduct 70% of the cost. IRS isn't stupid and this is a common audit trigger for home-based businesses.

One thing I haven't seen mentioned yet is the record-keeping aspect beyond just business use percentage. Make sure you keep the original receipt, warranty information, and any documentation showing when you placed the laptop into service for your business. The IRS wants to see the date you started using it for business purposes, not just when you bought it. Also, if you're planning to use Section 179, there's an income limitation - you can't deduct more than your business's taxable income for the year. So if your LLC only made $500 profit this year, you couldn't take the full $1050 Section 179 deduction. The unused portion would carry forward to next year though. For what it's worth, most small businesses I know go with Section 179 for items like laptops since the immediate deduction helps with cash flow, but definitely consider your overall tax situation and expected future income when making the choice.

As a tax professional who has helped many newly married couples navigate this exact situation, I want to emphasize a few key points that haven't been fully addressed yet: **Timing is crucial** - Since you just got married this month, you have the option to file as "Married Filing Jointly" for the ENTIRE 2025 tax year, even though you were only married for part of the year. This often works in your favor tax-wise. **Your tip income strategy** - With your $13.50/hour + tips job, I'd recommend tracking your tips more systematically going forward. The IRS expects tip reporting, and having good records will make your tax filing much smoother. For the withholding estimator, use a conservative estimate based on your recent months. **Quarterly check-ins** - Here's something most people don't think about: plan to revisit your withholding mid-year (around June/July) to see how you're tracking. Life changes, pay raises, or even seasonal variation in your tip income can throw off your initial calculations. **The "safe harbor" rule** - If you want extra peace of mind, you can aim to have withheld at least 90% of this year's tax liability OR 100% of last year's tax liability (whichever is smaller). This protects you from underpayment penalties even if you end up owing a bit. The IRS withholding estimator really is your best bet here. Just make sure to update it if anything significant changes with either of your jobs throughout the year!

Congrats on getting married! 🎉 I just wanted to chime in as someone who went through this exact same situation about 6 months ago. The overwhelm is so real - my spouse and I kept putting it off because it felt impossibly complicated. But honestly, after reading through this thread, you've gotten some absolutely fantastic advice here! The IRS withholding estimator really is a game-changer for multiple job situations like yours. One thing I'd add from my experience: don't beat yourself up if you don't get it perfectly right the first time. We were so worried about getting the "perfect" withholding that we delayed for months. In the end, we aimed for breaking even and ended up with a $200 refund - not perfect, but totally acceptable and way better than the stress of continuing to put it off. Also, your tip tracking situation is super relatable. I used to just estimate randomly, but now I use a simple app on my phone to log tips after each shift. Takes literally 10 seconds but makes such a difference when you need real numbers for tax stuff. The biggest thing that helped us was just scheduling a specific time to sit down together with all our paystubs and tackle the estimator. Once we actually started, it took way less time than we'd built it up to be in our heads. You've got this! 💪

I'm currently experiencing this exact same situation! Filed my return in early February, completed ID verification through ID.me on March 22nd, and WMR is still stuck on "Action Required" despite the IRS confirming my verification was successfully processed on March 25th when I called yesterday. It's incredibly frustrating not knowing what's happening, but reading through everyone's experiences here has been SO helpful. It seems like 2-3 weeks (or even longer) is completely normal for WMR to update after verification, and some people even received their refunds without WMR ever changing status! I was driving myself crazy checking it multiple times a day, but I'm going to try to follow the advice here about checking less frequently and maybe look into accessing my transcript for more accurate updates. Thank you to everyone who shared their timelines - it's such a relief to know we're all in this together waiting for these outdated systems to catch up!

I'm dealing with this exact same situation! Filed my return in early February, completed ID verification on March 15th, and WMR has been stuck on "Action Required" for weeks now. Called the IRS and they confirmed my verification was processed successfully on March 18th, but WMR still hasn't updated. It's been so stressful not knowing what's happening with my refund! But after reading through all these responses, I feel so much better knowing this is completely normal. Sounds like the WMR system is just incredibly slow to update after verification - some people waited 3+ weeks before seeing any change. I'm going to try to stop checking it obsessively and maybe look into getting my transcript access set up for more accurate information. Thanks for posting this question and thanks to everyone for sharing their experiences - it's such a relief to know we're all going through the same frustrating wait!