Has anyone actually calculated how much tax difference this makes? I'm in a similar situation but wondering if it's worth the effort to figure all this out vs just using what's on the 1099-B.

This is such a common issue that catches so many people off guard! I went through the exact same thing last year with my RSU sales. The key thing to remember is that you've already paid taxes on the RSU income when it vested, so you definitely don't want to pay again. One thing that really helped me was creating a simple spreadsheet to track everything. I listed each RSU vest date, the number of shares, and the fair market value per share on that date (which becomes your cost basis). Most equity platforms like Schwab or Fidelity will show this information in your transaction history or under "Tax Lots." Also, don't forget that if you sold immediately after vesting, you might actually have a small capital LOSS due to market fluctuations between vesting and selling. This can actually reduce your overall tax burden slightly. The paperwork is tedious but totally worth it - I saved about $8,500 in taxes by properly reporting my cost basis instead of accepting the $0 basis on my 1099-B. Form 8949 is your friend here, and make sure to use the correct codes for non-covered securities.

Has anyone used TurboTax to handle something like this? I'm in a similar situation but worried it won't handle the home sale loss correctly.

I'm dealing with a very similar situation right now - bought my house 10 months ago and need to sell due to my company relocating me. The advice here about primary residence losses not being deductible is spot on, but I wanted to add something that might help with your basis calculation. Make sure you're including ALL the costs that can be added to your basis, not just the obvious closing costs. Things like title insurance, recording fees, transfer taxes, and even some of the loan origination fees can be added to your purchase basis. On the selling side, realtor commissions, title fees, and other selling expenses reduce your realized gain (or increase your loss). Since you mentioned you're at around a $25k total loss after all expenses, you're definitely in personal loss territory that won't be deductible. But at least documenting everything properly will ensure you're not accidentally creating a taxable gain when you shouldn't have one. The job transfer angle mentioned by others is definitely worth exploring for the partial exclusion, even though you probably won't need it given your situation.

Has anyone here used TurboTax to handle the Form 8815 for excluding savings bond interest? I'm trying to figure out if their software handles this correctly or if I need to go to a professional this year. Never done this savings bond exclusion thing before and I'm a little nervous about messing it up.

Just wanted to add one important detail that I learned the hard way - make sure you understand the income phaseout limits before you commit to this strategy. The exclusion phases out completely for married filing jointly couples with MAGI over $175,200 (for 2025), and starts phasing out at $145,200. What caught me off guard was that the bond interest itself gets added to your MAGI when you redeem the bonds, which could potentially push you into or further into the phaseout range. So if you're close to that $145,200 threshold, make sure to calculate whether the additional bond interest will reduce or eliminate your exclusion. I almost made this mistake with about $15,000 in bond interest that would have pushed my MAGI too high. I ended up splitting the redemptions across two tax years to stay under the limit. Just something to keep in mind when planning your timing!

This is such a timely post! I've been dreading tax season because last year was my first time filing with freelance income on top of my regular W-2 job, and I had no idea what I was doing. I ended up paying way too much to have someone else handle it, but I never really understood what they did or why. An Excel spreadsheet that shows all the formulas and connections sounds perfect for someone like me who learns better by seeing how things work rather than just plugging numbers into a black box. I'm especially curious about how it handles Schedule C calculations for self-employment income - that's where I got completely lost last year. Does anyone know if this particular spreadsheet includes guidance or notes within the cells to explain what each calculation is doing? Sometimes Excel formulas can be just as confusing as the tax forms themselves if you don't have context for what they're supposed to accomplish. Also wondering about updates - tax laws seem to change every year, so how do you know if a spreadsheet is current with all the latest rules and rates?

This is exactly the kind of resource I wish I'd known about earlier! I've been using TurboTax for years but always felt like I was missing out on actually understanding my taxes. The black box approach works for getting things done, but it doesn't help you make better financial decisions throughout the year. I'm particularly interested in how comprehensive spreadsheets like this handle the interaction between different tax provisions. For example, I've never really understood how my HSA contributions affect my overall tax picture beyond just the immediate deduction, or how different types of investment income might push me into different tax brackets. One thing I'd love to know - does this spreadsheet include any kind of audit trail or documentation features? I'm always paranoid about being able to explain my calculations if the IRS ever has questions. With commercial software, you get those nice summary reports, but with a spreadsheet, I'd want to make sure I could easily show my work. Also curious if anyone has experience using these types of educational tools to help with tax planning for the following year? Once you really understand how all the pieces fit together, it seems like you could do much better "what-if" planning for things like Roth conversions or timing of capital gains. Thanks for sharing this - definitely going to give it a try!

This is exactly the kind of complex situation that requires specialized expertise beyond typical tax preparation. I've seen similar cases where families get trapped with appreciated assets in S-corps, and unfortunately there's no one-size-fits-all solution. One option you might not have explored yet is a charitable remainder trust (CRT) if you're charitably inclined. You could contribute some of the S-corp shares to a CRT, which would then sell the properties without immediate tax consequences to you, and you'd receive an income stream for life. This works especially well if you don't need all the property value immediately. Another consideration is whether any of the rental properties could qualify for opportunity zone deferrals if you're planning to reinvest. The timing with your father's passing might create some unique planning opportunities. Have you gotten a current appraisal on all four properties? Market conditions have changed significantly, and knowing exact current values versus basis will help determine which strategies make the most financial sense. Also, consider whether keeping one or two properties in the S-corp while extracting others might be a hybrid approach worth exploring. The key is running detailed projections on each option - sometimes paying the tax hit upfront is actually better than the ongoing complications and limitations of keeping everything in the S-corp structure.

I'm sorry for your loss and can understand how overwhelming this situation must be. You're dealing with one of the most challenging aspects of S-corp ownership - extracting appreciated real estate without massive tax consequences. One strategy worth exploring that hasn't been fully discussed is an installment sale back to the S-corp. Essentially, you could sell your shares back to the corporation over time, receiving payments spread across multiple years. This could help manage the tax impact by spreading recognition over several years instead of one large hit. Another angle to consider: since you inherited the shares, you might want to explore whether any portion of the properties could qualify for Section 1202 qualified small business stock treatment, though this typically applies to active businesses rather than rental properties. Given the complexity and the fact that you've already gotten conflicting advice from two accountants, I'd strongly recommend finding a tax attorney who specializes in S-corp restructuring rather than just a CPA. They'll be more equipped to handle the advanced strategies like the Section 368 reorganizations or other complex structures that could apply to your situation. Document everything carefully and consider getting multiple professional opinions before moving forward with any strategy. The stakes are too high to rely on uncertain advice, and the right solution could save you hundreds of thousands in taxes.