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.

I just went through this exact same situation last month! You're absolutely right to be proactive about getting this sorted out before filing. Since you withdrew the excess in December 2023 (same tax year), you've avoided the 6% excise tax penalty, which is the biggest hurdle. Here's what to expect: Your 1099-SA should show the withdrawal with Code 2 (excess contributions). On Form 8889, you'll report your total allowable HSA contribution (up to the 2023 limits) and then account for the excess withdrawal separately. The key is making sure you only claim the deduction for contributions up to the annual limit. One thing that caught me off guard - if your excess contribution earned any money while it was in your account (even just a few dollars), that earning portion will be taxable income that you'll need to report on Schedule 1. HealthEquity should provide a breakdown showing principal vs. earnings on your withdrawal. TurboTax handles this pretty well once you know where to look. In the HSA section, enter your total contributions first, then separately enter the excess withdrawal information. The software will calculate everything properly on Form 8889 for you. Since you caught this early and handled it correctly, you should be in great shape. Just keep all the documentation from HealthEquity about the withdrawal - that paper trail is important in case of any future questions from the IRS.

I'm dealing with a very similar HSA excess contribution situation right now, so this thread has been incredibly helpful! I changed jobs in July and didn't realize both employers were contributing until I was already over the limit by about $900. One thing I wanted to add that I learned from my HR department - some companies use different HSA contribution timing. My old employer front-loaded their annual contribution in the first quarter, while my new employer spreads it out monthly. This made it really hard to track until I was already way over the limit. I'm planning to request the excess withdrawal before December 31st based on all the advice here. Does anyone know if there's a specific form I need to fill out for HealthEquity, or can I just call them directly? I want to make sure I get this processed in time to avoid any taxable earnings on the excess amount. Also, for those who've been through this - did you notify your current employer about the excess contribution situation? I'm wondering if I should adjust my ongoing HSA contributions for the rest of the year to prevent this from happening again in 2024.

Glad to hear you got everything sorted out! For anyone else facing similar time constraints with tax document retrieval, I'd recommend having multiple backup plans in place. One thing that's often overlooked is checking if your accountant or tax preparer has copies of these forms on file. Many CPA offices maintain client records for several years and can provide certified copies much faster than going through the IRS or trying to reconstruct them from your accounting software. Also, if you're using QuickBooks Desktop, make sure you're regularly backing up your company files with the year included in the filename (like "MyCompany_2022.qbw"). This makes it much easier to access historical data when situations like PPP documentation requests come up. The newer cloud-based versions handle this automatically, but desktop users need to be more proactive about maintaining these archives.

As someone who's dealt with similar documentation challenges for business loans, I want to emphasize how important it is to establish good record-keeping practices before you need them urgently. One additional tip that hasn't been mentioned yet: if you're using QuickBooks Desktop and have been backing up to external drives or cloud storage, check those backup locations for older company files. Sometimes people forget they have complete historical data stored there that can be opened in read-only mode to access old reports and forms. Also, for future reference, consider setting up a simple filing system where you save PDF copies of important tax forms immediately after filing them each quarter/year. Create folders like "2024_Payroll_Tax_Forms" and save copies there as soon as you generate them in QuickBooks. This creates a secondary archive that's independent of your accounting software and can be a lifesaver when you need quick access to historical documents. It sounds like you found a good solution with the combination of approaches mentioned in this thread. The key takeaway for other business owners is to not rely on just one method for accessing critical tax documents - having multiple backup strategies makes these urgent requests much less stressful to handle.