This is such a helpful thread! I'm starting as a cocktail server at a casino next month and had similar concerns about GITCA. Reading everyone's experiences really puts my mind at ease that it's a legitimate program. One question I haven't seen addressed - does GITCA affect how much tax is withheld from my regular paychecks? I'm wondering if I should adjust my W-4 withholdings or if the casino automatically handles the tax withholding on the allocated tip amounts. I want to make sure I don't end up owing a bunch at tax time or getting a huge refund because my withholdings were off. Also, does anyone know if GITCA rates vary significantly between different casinos, or are they pretty standardized across the industry for similar positions?

Just wanted to jump in as someone who's been through this exact situation! I started at a tribal casino about 18 months ago and had the same concerns about GITCA sounding "too good to be true." What really helped me understand it was realizing that GITCA isn't about avoiding taxes - you still pay the same amount of taxes on your tip income. It's more like having the IRS pre-approve a reasonable estimate of what someone in your position typically earns in tips, so you don't have to prove every single dollar you made. The "won't be audited" part your manager mentioned is a bit of an oversimplification. You're protected from tip-specific audits as long as you're reporting at the agreed GITCA rates, but you could still potentially be audited for other reasons (like if you have other income sources or tax situations that raise flags). I'd definitely recommend asking your payroll department for a written explanation of how GITCA works at your specific casino, including what the allocated rates are for your position. That way you can make an informed decision and understand exactly what you're signing up for. The peace of mind and simplified record-keeping has been totally worth it for me!

This is actually a common concern that many taxpayers have when they first encounter TurboTax's auto-import feature. The system works through partnerships with major payroll processors like ADP, Paychex, and others. When your employer processes your W-2 through these services, the data becomes available in a shared database that TurboTax can access once you verify your identity. The key thing to understand is that you likely consented to this during account setup, though it's buried in the terms of service. The IRS also has regulations around this type of data sharing for tax preparation purposes, so it's not completely unregulated. If you're uncomfortable with this, you can disable the auto-import feature in your account settings under "Profile & Account" > "Import Settings." Just keep in mind you'll need to manually enter all your tax documents if you turn it off. Also worth checking this setting each year since TurboTax sometimes resets preferences when they update for the new tax season.

This auto-import feature caught me off guard too when I first used TurboTax! What helped me understand it better was realizing that this is actually part of a broader trend in the tax industry toward "pre-populated" returns, similar to what many other countries already do. The IRS has been working on initiatives to make tax filing easier through programs like "Return Free Filing" where your tax information would be pre-filled by the government itself. TurboTax's auto-import is essentially a private sector version of this concept. If you're still concerned about privacy, you might want to consider that the same W-2 data is already being shared with the IRS, Social Security Administration, and state tax agencies automatically by your employer anyway. TurboTax is just tapping into an existing data flow rather than creating a new one. That said, it's totally valid to want more control over your data. The manual entry route gives you complete oversight of what information goes into your return, even if it takes a bit more time.

I went through this exact same nightmare last year! What finally worked for me was requesting an "escrow analysis" statement directly from my mortgage servicer - this is different from your regular mortgage statements and shows a detailed breakdown of all payments made from your escrow account throughout the year. Most servicers are required to provide this annually, but you can request it specifically. It will show every property tax payment made, even if your 1098 shows zero. I had to escalate past the first-level customer service (they didn't even know what I was talking about), but once I got to someone in the escrow department, they sent it right over. Also, keep your closing documents handy - they often show prorated property tax amounts that you paid at closing, which are also deductible but easy to overlook. Between the escrow analysis and closing docs, I found over $4,200 in deductible property taxes that weren't on my 1098.

This is such a common and frustrating issue! I went through the same thing when we refinanced our home mid-year. Here's what I learned from my CPA: the 1098 only reports what the lender considers "qualified" property tax payments, and sometimes there are timing issues or coding errors on their end. Your best bet is to get a complete payment history from your county tax collector's office (not just the assessor). They can provide an official statement showing all property tax payments made on your properties during the tax year, regardless of who made them. Most counties now have online portals where you can download these reports instantly using your property address or parcel number. Don't forget about the property taxes you may have prepaid at closing for your new home, or any prorated amounts you were credited for when you sold your old home. These are often overlooked but are legitimate deductions. The key is having documentation that shows the taxes were actually paid during the tax year - the IRS doesn't care that your 1098 is wrong, they just need proof the payments were made.

As a tax professional, I want to emphasize something important that hasn't been fully addressed - the timing of when your boss can make the S-corp election for it to be effective this year. If he wants the S-corp status to apply to the entire 2025 tax year, he needs to file Form 2553 by March 15, 2025 (2 months and 15 days after the beginning of the tax year). If he files after that deadline, the election won't be effective until January 1, 2026. This is crucial because if he's already been taking "salary" payments in 2025 but the S-corp election isn't effective until 2026, ALL of those payments for 2025 will need to be treated as owner draws for tax purposes, regardless of how they were processed through payroll. Also, once he makes the S-corp election, he'll need to obtain an EIN if the PLLC doesn't already have one, set up proper payroll withholding, and start making quarterly payroll tax deposits. The "reasonable salary" requirement is real - the IRS has been cracking down on S-corp owners who try to minimize their salary to avoid payroll taxes. Given the complexity and potential penalties for getting this wrong, I'd strongly recommend having a qualified tax professional handle the transition, especially since he's already taken payments this year that need to be properly classified.

I've been following this discussion and want to add a practical perspective as someone who handles payroll for several small businesses. One thing that often gets overlooked is the quarterly payroll tax filing requirements once you make the S-corp election. As an S-corp, your boss will need to file Form 941 quarterly and make federal tax deposits (often monthly or semi-weekly depending on the payroll amount). This is in addition to state payroll tax requirements. Miss these deadlines and you're looking at penalties that can quickly eat into those self-employment tax savings everyone's talking about. Also, regarding the "reasonable salary" discussion - I've seen the IRS audit several S-corp owners in our area, and they seem to focus on businesses where the salary is less than 40-50% of the business profit. While there's no hard rule, that seems to be a red flag threshold. For a law practice with $150k profit, paying a $40-50k salary and taking the rest as distributions would probably be defensible, but paying $25k and taking $125k in distributions would likely attract unwanted attention. The paperwork burden is real - beyond just the tax return complexity, you're now dealing with W-2s, payroll tax returns, and proper documentation requirements. Make sure your boss factors in the time cost of all this additional compliance work when calculating whether the tax savings are worth it.

This is such a helpful thread! I'm dealing with a similar situation where I left my company last year and just sold some ESPP shares. One thing I wanted to add for anyone else in this boat - make sure to check if your old company switched payroll providers or got acquired after you left. I spent weeks trying to get my old W-2s from my former employer's HR, only to find out they had been acquired and all the payroll records moved to a different system. I finally had to request copies directly from the IRS using Form 4506-T, which took about 10 days but was totally worth it to get the exact compensation amounts that were reported. Also, if you're having trouble finding the ESPP compensation on your W-2, sometimes it's not in Box 14 like others mentioned. On mine it was actually included in Box 1 (wages) and I had to look at my final paystub from that year to see the breakdown of regular wages vs. ESPP compensation. Just another place to check if you're coming up empty!

This thread has been incredibly helpful! I'm in a similar situation where I left my job at a tech company about 8 months ago and just sold some ESPP shares. One thing I learned the hard way is to double-check the cost basis calculation even if your broker provides a "Supplemental Information Statement" like Emily mentioned. I found that Schwab had the right compensation amount but applied it to the wrong lot of shares (I had multiple purchase periods). This would have resulted in me overpaying taxes on some lots and underpaying on others. What I ended up doing was creating my own reconciliation spreadsheet using Yuki's method above, then cross-referencing it with both my 1099-B and the supplemental statement. Found a $400 discrepancy that would have cost me about $150 in extra taxes! Also want to second the recommendation about keeping detailed records going forward. I set up a simple Google Sheet now that automatically calculates the discount amount and tracks holding periods. Takes 5 minutes after each ESPP purchase but will save hours during tax season.