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!

Has anyone dealt with leaving a company but negotiating an extension on the exercise period? Most standard option agreements only give you 90 days after leaving to exercise, but I've heard some companies are flexible on this, especially when options are underwater.

One additional consideration that might help with your decision - if you're planning to leave the company anyway, you could potentially negotiate with your employer to extend the exercise window beyond the typical 90-day post-employment period. This would give you more time to see how the company performs with that Q3 product launch you mentioned. Also, make sure you understand exactly what type of options you have (ISO vs NSO) as this affects the tax treatment. With ISOs, you generally have better tax advantages if you hold the stock for at least one year after exercise and two years after grant date to qualify for long-term capital gains treatment. Given that you're essentially guaranteed a loss if you exercise now, it might be worth having a conversation with your company about either repricing the options to current FMV or extending your exercise window. Many companies are becoming more flexible about this, especially in situations like yours where the employee would be financially penalized through no fault of their own.

As someone who recently navigated a similar non-resident alien tax situation, I wanted to share a few practical tips that helped me get through the HSA and IRA filing process. For the Form 8889 issue with Sprintax - I found it helpful to complete the Sprintax return first, then print out a draft to see exactly where the HSA deduction should flow. The key is making sure the deduction amount from Form 8889 gets properly reflected on Schedule 1, Line 13, and then recalculating your AGI manually. I used a simple spreadsheet to track the adjustments and make sure everything balanced. One thing I learned the hard way - if you're filing electronically through Sprintax, you'll need to print and mail your return anyway once you attach the manual Form 8889. The IRS systems can't process mixed electronic/paper filings, so you lose the e-file option. For the IRA deduction question - since you mentioned you're on a TN visa from Canada, you should definitely be eligible for the deduction assuming you meet the income requirements. The US-Canada tax treaty actually has favorable provisions for retirement savings. Just make sure you're not also claiming RRSP contributions in Canada for the same income, as that could create treaty complications. One final tip - keep detailed records of all your manual calculations and adjustments. If the IRS has questions later, you'll want to be able to show exactly how you arrived at your numbers.

I wanted to add another perspective as someone who dealt with a similar HSA/IRA situation as a non-resident alien. One thing that caught me off guard was the timing requirements for HSA contributions versus when you can actually claim the deduction. Even though you can contribute to your HSA through April 15th for the previous tax year, if you're manually filing Form 8889 with your non-resident return, you'll want to make sure all contributions are actually completed before you file. Unlike regular filers who might estimate and adjust later, the manual process makes corrections much more complicated. For your IRA situation on the TN visa - definitely confirm your contribution limits based on your earned income. As a non-resident alien, you can only contribute up to 100% of your US earned income or the annual limit ($7,000 for 2024), whichever is less. This is different from residents who might have other forms of compensation that count. Also, one practical tip for the Sprintax + manual Form 8889 approach - complete everything in Sprintax first, then print the entire return. Fill out Form 8889 separately, and physically attach it to the printed return before mailing. Don't try to modify the Sprintax PDF directly as it can cause formatting issues that might confuse IRS processing. The manual recalculation process mentioned by others is definitely doable - I found it helpful to work backwards from the final tax owed to make sure my adjustments were correct.