Just wanted to add that the timing of when all those K1s arrived matters too. If most came in late (which is common with complex partnerships), the accounting firm probably had to file extensions and do a lot of the work during their non-busy season. That's often billed at different rates. My firm charges 20-30% more for K1-heavy returns because they're unpredictable and often cause bottlenecks in our workflow. The 60-70 new K1s would definitely add setup time too.

As someone who's dealt with complex returns (though nowhere near your sister's level), I'd echo what others are saying - $19,500 for that complexity actually sounds quite reasonable. One thing I'd suggest is asking the firm for a breakdown of how they arrived at that fee. Most reputable firms should be able to show you time spent on different components - K1 processing, state return prep, review time, etc. This transparency helps you understand what you're paying for and can be useful for budgeting future years. Also, given the scale of her investments, your sister might want to consider working with the firm throughout the year for tax planning rather than just at filing time. With that income level and complexity, proactive planning could potentially save more in taxes than the additional advisory fees would cost. Many firms offer quarterly check-ins for clients with situations like this.

One thing I haven't seen mentioned yet is the importance of keeping your LLC's investment activities clearly documented and separate from any personal trading you might do. Even though both end up on your personal Schedule D for a disregarded entity, you'll want to maintain clear records showing which transactions were made through the LLC versus any personal accounts. This becomes especially important if you have both LLC and personal investment accounts with the same brokerage. I'd recommend using separate brokerages if possible, or at minimum keeping very detailed records that clearly identify the source of each transaction. If you ever get audited, the IRS will want to see that you maintained proper separation between your business and personal activities, even though they're taxed the same way. Also, since you mentioned your accountant disappeared, you might want to consider finding a new CPA before next year's tax season starts. Having professional guidance becomes even more valuable as your LLC grows or if you start generating more complex investment income. The peace of mind is worth the cost, especially when dealing with business entity taxation rules that can change or have nuances you might miss filing on your own.

One additional consideration I haven't seen mentioned yet is the potential impact on your LLC's operating agreement if you're doing significant investment activity. While the tax treatment for a disregarded entity is straightforward (everything flows to your personal return), you'll want to make sure your operating agreement properly addresses investment activities if that wasn't originally contemplated when you formed the LLC. Some operating agreements are written very narrowly and might not explicitly allow for investment activities beyond the LLC's primary business purpose. If you plan to continue trading through the LLC, it's worth having an attorney review your operating agreement to ensure it gives you the authority to engage in investment activities and that any liability protections you're seeking are properly structured. Also, depending on the volume and frequency of your trading, you might want to consider whether you need to register for any additional business licenses or comply with securities regulations in your state. Most casual investing doesn't trigger these requirements, but if you're doing substantial trading activity through a business entity, there could be additional compliance considerations beyond just the tax reporting we've been discussing. Better to address these structural issues now while your investment activity is relatively new rather than trying to fix them later if your trading becomes more substantial or complex!

Has anyone tried Drake Tax Software for S-Corps? My CPA uses it and suggested I might want to try the prosumer version for my small S-Corp.

I've been filing S-Corp returns for my consulting business for about 3 years now and have tried most of the major software options. Here's what I wish someone had told me when I started: For your first year, I'd actually recommend starting with TurboTax Business despite the higher cost. Yes, it's more expensive, but the interview process is really thorough and educational. It explains WHY certain deductions apply to S-Corps and helps you understand the underlying concepts, not just fill out forms. Once you're comfortable with S-Corp tax concepts (probably by year 2 or 3), then switch to TaxAct to save money. I made that transition and it worked well because by then I understood what I was looking for. One critical tip regardless of software: make sure you're paying yourself a "reasonable salary" through payroll before taking distributions. This is the #1 mistake I see new S-Corp owners make, and it can trigger an audit. The software won't necessarily warn you about this ratio, so it's worth discussing with your tax advisor even if you're filing yourself. Also, keep detailed records of all business expenses throughout the year - don't wait until tax time to organize everything. Both TurboTax and TaxAct are only as good as the information you put into them.

I'm gonna go against the grain here... Just use FreeTaxUSA or Cash App Taxes (formerly Credit Karma Tax). Both handle investments including stock sales and dividends. FreeTaxUSA is free for federal and like $15 for state. Cash App Taxes is completely free for both federal and state. I switched from TurboTax to FreeTaxUSA two years ago when my taxes got more complicated with investments and rental property. Saved over $120 and the process was actually easier! TurboTax is just really good at making you think you need their expensive versions when you don't.

As someone who's been through a similar transition from simple W-2 filing to dealing with investments, I'd recommend starting with the document analysis approach others mentioned. Understanding exactly what forms you'll need is crucial before choosing software. For your specific situation - multiple W-2s, stock sales, dividends, and retirement accounts - you're definitely looking at needing investment-capable software. The key distinction is that selling stocks requires Schedule D and Form 8949, which kicks you out of basic versions of any tax software. Your 403b contributions should already be reflected on your W-2 (look for box 12 with codes like D, E, F, G, or H), so that part is actually straightforward. The Roth IRA contributions typically don't need to be reported unless you qualify for the Saver's Credit, which at 19 you might depending on your income level. Between TurboTax Premier and the alternatives like FreeTaxUSA or Cash App Taxes, it really comes down to how much hand-holding you want. TurboTax is more expensive but walks you through everything step-by-step. The alternatives can save you $100+ and handle the same forms, but assume you're comfortable reading instructions and answering questions without as much guidance. Given this is your first year with investments, you might appreciate TurboTax's explanations this time around, then switch to a cheaper alternative next year once you understand the process better.

I handle payroll for a company that does relocation grossups and this is normal. Your W-2 will show the TOTAL - both the $15k you received plus the additional amount the company paid in taxes on your behalf. The full amount is taxable income. Check your last paystub of the year and look at the "YTD" column for federal withholding. It should be higher than normal because of the extra withholding for the relocation. If your company did the gross-up correctly, they would have withheld around 22% federal (supplimental rate) plus Medicare/SS taxes on the full grossed-up amount. If TurboTax is saying you owe more, it might be because your overall tax bracket is higher than 22% so you need to pay the difference.

As a newcomer to this community, I really appreciate all the detailed explanations here! I'm dealing with a similar situation where my employer offered a relocation package, but I haven't accepted the job yet. Reading through these comments, it sounds like the tax implications are pretty complex. For someone who hasn't gone through this before, would you recommend negotiating for the company to handle the relocation expenses directly with vendors instead of giving me a lump sum? Or does it not really matter since either way it ends up being taxable income? Also, are there any questions I should ask HR upfront to make sure I understand exactly how they calculate the gross-up and what will show up on my W-2? I'd rather avoid the confusion that several people here experienced!