Don't forget about the Net Investment Income Tax (NIIT) of 3.8% that kicks in for higher incomes. So some people actually pay 23.8% not just 20% on their capital gains!

This is such a helpful thread! I'm dealing with a similar situation where I'm planning to sell some rental properties next year. One thing I haven't seen mentioned yet is the depreciation recapture rules - if you've been claiming depreciation on rental property, you'll owe tax at 25% on the depreciation amount you claimed, even if the rest of your gain qualifies for the lower capital gains rates. Also, for anyone considering the charitable donation strategy mentioned earlier, don't forget about donor-advised funds. You can make a large charitable contribution in one year to lower your AGI for capital gains purposes, but then distribute the funds to actual charities over several years. It gives you more flexibility while still getting the immediate tax benefit. The timing advice from Emma is spot-on too. I've been working with my CPA to spread out my property sales over 2-3 years to stay in lower tax brackets rather than selling everything at once and getting hit with the highest rates.

My company offers $150/month for transit and they don't withhold taxes either. My accountant said as long as it's under the IRS limit and used for qualified transportation, I'm good. The 2025 limit is like $300 I think?

I've been dealing with a similar situation at my company and wanted to share what I learned after doing some research. The tax treatment really depends on HOW your employer is providing these rideshare reimbursements. If they're treating it as a "commuter benefit" under IRS Section 132(f), then up to $300/month (for 2025) can be tax-free. However, many employers mistakenly think all rideshare reimbursements automatically qualify, but the IRS has specific rules about what counts as "qualified transportation." For rideshares to qualify as tax-free, they generally need to be part of a formal commuter benefit program and used for specific purposes like getting to/from transit stations or for carpooling arrangements. Just regular Uber/Lyft rides from home to work usually don't qualify unless there are special circumstances. Since you mentioned it's showing up on your paystub without taxes withheld, I'd double-check with your HR department about how they're coding this benefit. You might also want to keep records of exactly what these rides are for, just in case you need to justify the tax treatment later.

Just a suggestion - if you're concerned but like your accountant otherwise, maybe suggest an alternative? Ask if you can come to their office and show the cards in person instead of providing copies. A legitimate accountant shouldn't have a problem with this option.

This is definitely not normal and I'd be very cautious about this request. As others have mentioned, legitimate tax preparers don't need to keep copies of Social Security cards on file - they only need the numbers for filing purposes. Since you've been working with this accountant for 3 years, I'd recommend having a direct conversation about what specifically changed in their process to suddenly require this documentation. A few questions to ask: 1. What specific security concern prompted this new requirement? 2. Why do they need physical copies when they already have your SSNs on file? 3. How will these copies be stored and protected? 4. Would they accept in-person verification instead of copies? If they can't provide clear, satisfactory answers to these questions, that's a major red flag. The fact that this is a sudden change after years of working together is particularly concerning. Trust your instincts here - if something feels off, it probably is. You might also want to check if your state has specific regulations about tax preparer document retention requirements. Many states actually prohibit keeping unnecessary copies of sensitive documents like Social Security cards.

You might want to look into whether you qualify as an independent contractor rather than an employee. Many PCAs are actually misclassified. If you're actually an independent contractor, you'd handle your own taxes through quarterly estimated payments anyway, and this might simplify things for you going forward. The IRS has a form called SS-8 that helps determine proper worker classification. Worth looking into since your intermediary is already failing at basic employer responsibilities!

I'm dealing with a similar situation right now and wanted to share what I've learned from calling the IRS directly. When your employer fails to withhold taxes despite proper W-4 submission, you can actually request what's called a "lock-in letter" from the IRS. This is a formal notice that the IRS sends to your employer specifying exactly how much must be withheld from your paychecks. To get this, call the IRS at 1-800-829-1040 and ask for the "employee protection" department. You'll need to provide documentation that you submitted proper W-4 forms and that your employer ignored them. The IRS takes this pretty seriously since employers are legally required to follow valid withholding instructions. Also, since you're working through DSS as a PCA, you might have additional protections under your state's labor laws. Many states have specific regulations about how fiscal intermediaries must handle payroll for state-funded positions. I'd recommend contacting your state's Department of Labor wage and hour division - they often have more teeth than just complaining to DSS directly. Keep fighting this! You shouldn't have to bear the burden of your employer's failure to follow basic tax laws.

Have you considered what the 846 code actually means in this process? It's simply the IRS saying "we've approved your refund and scheduled it." The money doesn't instantly move at that moment. What typically happens is the Treasury sends these in batches to the ACH network, which then distributes to financial institutions. Cash App's advantage is they don't wait for final settlement before showing the money in your account. I filed on January 15th and had an 846 date of February 3rd. The money appeared in my Cash App on February 1st around 2pm. But would I make financial plans assuming this will happen? Probably not. Is an extra day or two worth risking an important investment decision? That's the real question you should be asking.

Based on my experience with Cash App over the past few years, they do tend to release tax refunds early - usually 1-2 days before the 846 date. However, since you're making a time-sensitive investment decision, I'd strongly recommend having a backup plan. The timing isn't 100% guaranteed, and the difference between getting your money on 2/24 versus 2/26 could impact your investment window. Have you considered reaching out to Cash App support directly to ask about their typical processing time for tax refunds? They might be able to give you a more definitive answer about when to expect the deposit. Also, just curious - what type of investment has such a tight deadline? Sometimes there are ways to structure deals with contingencies if funding timing is uncertain.