I'm still confused about one thing - if I have wash sales throughout the year but close out ALL my positions by December 31st and don't rebuy for 30+ days, do I still get to claim all my net losses for the year?

As someone who went through this exact same confusion last year, I can tell you that you're likely overthinking it. With $54k in gains and $49k in losses, you're probably looking at paying taxes on roughly your $5k net profit, not the full $54k. The wash sale rule doesn't eliminate your losses - it just defers them by adding them to the cost basis of your replacement shares. Since you're day trading the same stock constantly, those adjusted cost bases are getting realized when you sell those shares throughout the year. The real trap is if you have significant wash sale losses at year-end that carry into January. That's when you could get stuck paying taxes on gains while having your losses deferred to next year. My advice: Track your actual realized gains/losses carefully (not just the gross numbers), and if you're worried, consider using one of the software tools mentioned above to get a clearer picture of your true tax situation. Don't panic - you're probably in better shape than you think!

This thread has been incredibly helpful! I'm in a similar boat - retired last year and trying to navigate the tax implications of living off investment income. Just wanted to add one more consideration for folks in this situation: even though you don't have to make estimated payments with zero prior year liability, it might still be worth making voluntary payments if you expect a large tax bill. The IRS doesn't charge penalties, but you're essentially giving yourself an interest-free loan to the government for the year. I've been setting aside about 20% of my capital gains in a high-yield savings account so I can earn some interest on the money rather than sending it to the IRS early. When April comes around, I'll have the tax money plus a little extra from the interest earned. Just another way to think about it!

This has been such a valuable thread! I'm also recently retired and was completely overwhelmed trying to figure out estimated taxes for the first time. Like many others here, I had zero tax liability last year but was panicking about quarterly payments after some recent stock sales. The confirmation from multiple sources about the safe harbor rule is incredibly reassuring. What really stands out to me is how many people mentioned the same struggle - getting conflicting information or being disconnected during IRS calls. It's clear this is a common pain point for new retirees. I'm particularly grateful for the practical tips about setting aside money in a high-yield savings account rather than making voluntary payments. As someone who's always been conservative with money, I was leaning toward making estimated payments "just to be safe," but the opportunity cost argument really makes sense. Why give up 4-5% interest when I'm not required to make the payments? The resources mentioned here (taxr.ai for projections and Claimyr for IRS calls) sound really helpful for someone like me who wants professional guidance but doesn't want to pay full CPA fees for every question. One question for the group - for those who've been doing this for a while, do you find it gets easier to estimate your annual tax liability once you have a year or two of retirement tax returns under your belt? I'm hoping this uncertainty is just part of the learning curve!

Just to give a different perspective - I tried doing my S-Corp taxes with TurboTax Business last year and deeply regretted it. Spent 20+ hours struggling through it, thought I'd done everything right, and still got notices from the IRS about missing forms 6 months later. Had to hire a CPA to fix everything anyway and ended up paying way more than if I'd just gone to them in the first place.

As someone who's been through the exact same transition from W-2 to S-Corp, I'd definitely recommend going the CPA route for your first year. The complexity isn't just in filing the returns - it's understanding all the ongoing compliance requirements that TurboTax won't teach you. Since you mentioned you've only been taking owner's draws instead of paying yourself a salary, you're going to need professional help to sort that out anyway. The IRS is pretty strict about S-Corp owners paying themselves reasonable compensation through payroll, and getting that wrong can trigger audits or penalties. One thing I wish someone had told me: start interviewing CPAs now, not in March when everyone's swamped. Many good ones are already booking up for tax season. Look for someone who specializes in small business and can explain things clearly - you want to learn the process, not just hand everything off blindly. The investment in professional guidance your first year will save you headaches (and probably money) down the road. Once you understand the S-Corp requirements and have proper systems in place, you can always consider doing simpler years yourself later.

If you're comfortable doing a bit more work yourself, you could try using the Free Fillable Forms directly from the IRS. It's not as user-friendly as the guided options like TurboTax, but it's completely free and handles all forms including 1099-NEC. You just need to know which forms to fill out and how to do the calculations yourself.

Another option worth considering is TaxSlayer's Simply Free edition - it handles both W-2 and 1099-NEC forms without any upgrade fees for federal filing. I used it last year when I had a similar contractor-to-employee situation and it walked me through everything step by step. The interface is pretty straightforward and they don't hit you with surprise charges at the end like some other services do. State filing does cost extra (around $30) but federal is genuinely free even with 1099 income. Just make sure you're using the "Simply Free" version and not their regular free trial which does have limitations.

3 Has anyone actually been audited over their Accountable Plan? I've been reimbursing employees for home office equipment, internet, and occasional coffee shop visits for years with no issues. As long as they provide receipts and a business justification, I've approved them under our Accountable Plan per Treas. Regs. §1.62-2(d).

The distinction between repairs and improvements is crucial here, and I'd be very conservative with both scenarios you've described. For the HVAC system, this is clearly a capital improvement that increases the home's value permanently. Even though 12% is used for business, the IRS will likely view this as primarily benefiting the employee as a homeowner. I'd avoid reimbursing this under your Accountable Plan - it's exactly the type of expense that gets flagged in audits and reclassified as taxable compensation. For the coffee shop visits, the key question is business necessity. Can the employee document why they couldn't work from their home office that day? "I like the atmosphere" won't cut it - you need legitimate business reasons like client calls requiring a quiet background, internet outage at home, or specific work that benefits from a different environment. Even then, food/beverage costs are subject to the 50% meal limitation and need detailed documentation. My recommendation: Create a clear written policy defining what qualifies before approving any reimbursements. For home office expenses, stick to supplies, equipment, and utilities rather than improvements. For alternative workspace costs, require written justification for each occurrence explaining the business necessity.