Sorry to jump in with a slightly different perspective, but isn't renting a different car each week extremely inefficient tax-wise? The standard mileage rate for 2024 is around 67 cents per mile, which accounts for ALL vehicle costs including depreciation. If you're paying $15,600 annually for rentals, you'd need to be driving nearly 23,300 business miles annually to make that worthwhile compared to just using your own vehicle and taking the standard deduction. Have you calculated if this approach actually makes financial sense?

You might also want to consider whether your photography business would benefit from a dedicated business vehicle instead of weekly rentals. As a fellow creative professional, I understand wanting to protect your personal car from wear and tear, but there could be more tax-efficient approaches. For example, you could lease a vehicle exclusively for business use and deduct 100% of the lease payments, or purchase a used vehicle and depreciate it over time. This would eliminate the need to track personal vs. business use percentages entirely. That said, if the rental approach works best for your workflow (maybe you need different vehicle sizes for different shoots?), just make sure you're documenting everything meticulously. The IRS can be particularly scrutinous of Schedule C vehicle deductions, so having ironclad records is crucial. Consider setting up a simple system where you log business purpose, mileage, and take photos of receipts immediately after each rental period. Also, don't forget about other deductible expenses related to your vehicle use - things like GPS apps, car phone mounts, or other equipment you need for business travel can also be deducted as business expenses.

Have you guys considered splitting the benefits? Like one of you claims the child tax credit and the other claims the EIC if eligible? My ex and I alternate years claiming our kid which works for us.

This is such a common situation for unmarried couples with kids! From what you've described, it sounds like your boyfriend would likely be the better choice to claim your child since he has the higher income and provides the financial support. The IRS tiebreaker rules for unmarried parents living together typically favor the parent with higher AGI. However, don't overlook the Earned Income Credit (EIC) - even with your lower income of $27k, you might still be eligible for EIC if you claim your child, and sometimes that can be more valuable than the Child Tax Credit your boyfriend would get. The EIC is specifically designed to help lower-income working families and phases out at higher incomes. My suggestion would be to use tax software or consult a professional to run both scenarios - him claiming vs you claiming - and see which gives your household the better overall refund. Sometimes the math isn't as obvious as it first appears, especially when factoring in all the different credits and filing statuses available to each of you. Also keep in mind that whichever one of you doesn't claim the child will need to file as Single rather than Head of Household, so factor that into your calculations too. Good luck navigating your first tax season as parents!

I work in payroll and deal with this regularly. One thing nobody's mentioned - if the employee had any accrued vacation payout or final wages paid AFTER death, those should be treated differently tax-wise. Those payments go on a 1099-MISC to the estate or beneficiary, not on the W-2. Also, ask for the death certificate copy for your records - you'll need it. In Texas, if they're claiming common law marriage, have them complete a Declaration of Informal Marriage form (it's a Texas state form) if they haven't already filed one with the county clerk.

I'm sorry for your loss and the difficult situation you're navigating. This is definitely a complex area that requires careful attention to both federal and Texas state requirements. A few additional points that might help: **Timing considerations:** Since it's already December and the husband is asking about the W-2, you might want to proactively communicate the standard January 31st deadline for W-2 distribution. This can help manage expectations while you're gathering the proper documentation. **Documentation for common law marriage:** In addition to what others mentioned, Texas recognizes common law marriage if three elements are met: (1) they agreed to be married, (2) lived together in Texas as spouses, and (3) represented themselves publicly as married. Evidence could include joint utility bills, insurance policies listing each other as spouses, joint bank accounts, or sworn affidavits from friends/family who knew them as a married couple. **Estate considerations:** Even if you determine they weren't legally married, the W-2 still needs to be issued - it would just go to whoever is handling the estate (could be a parent, sibling, or court-appointed administrator). **Record keeping:** Make sure to document whatever verification process you use for your company's records. This protects you if questions arise later from other family members or during any potential audit. Consider reaching out to your company's legal counsel or tax advisor if you have access to one, especially given the complexity around the marriage status verification.

I work in benefits administration (not tax advice!) and this issue comes up frequently. The technical distinction I've seen most HSA administrators make: 1. Items that ONLY serve a medical purpose = eligible 2. Items with dual purpose = not eligible So breast pumps = eligible because their only purpose is medical Specialized breast milk storage bags = usually eligible because they're designed specifically for breast milk General bottles = usually not eligible because they can be used for formula, water, etc. But honestly, every HSA administrator interprets things a bit differently, and some are more lenient than others. It's always best to check with your specific administrator.

Thank you all for sharing your experiences! This has been incredibly helpful. Based on what everyone is saying, it sounds like the key is: 1. Breast milk storage bags specifically marketed for breast milk = likely eligible 2. General bottles = likely not eligible unless part of pump kit 3. Each HSA administrator has different interpretations I think I'm going to start by purchasing the Medela or Lansinoh storage bags that several of you mentioned getting approved, and skip the bottles for now. If we do need bottles later, I'll look for ones that are specifically part of a pumping system. @Sofia Ramirez and @StarSeeker - I'm definitely going to check out taxr.ai before submitting anything. Having documentation that explains the eligibility seems like it could save a lot of headaches. @Ava Martinez - I'll also keep Claimyr in mind if I run into issues and need to actually talk to someone at my HSA company. The hold times are brutal! Really appreciate this community helping navigate these confusing rules. It's frustrating that something so clearly related to medical care (breastfeeding) has so many gray areas, but at least now I have a better strategy going in.

One thing nobody mentioned - check if any of the shares were ever sold over the years or if all dividends were reinvested. Sometimes with these old custodial accounts, dividends get automatically reinvested which affects your basis. Also if the company was acquired or had spinoffs during that time period you'll need to account for that too.

I dealt with a very similar situation a few years back with inherited stock from my grandfather's employee options at IBM in the 1980s. One resource that helped me tremendously was the IRS Publication 550 (Investment Income and Expenses), which has specific guidance on basis calculations for gifted securities. The key thing to remember is that you need to establish your father's "adjusted basis" at the time of the gift, not just what he originally paid. This includes the exercise price PLUS any compensation income he reported on his W-2 when he exercised the options. If you're still missing records, try contacting the plan administrator (usually the company's HR department or their third-party benefits provider). Even decades later, they sometimes maintain records of employee stock option exercises, especially for larger companies. They might be able to provide a statement showing the exercise date, number of shares, exercise price, and fair market value at exercise. Also keep detailed documentation of your efforts to reconstruct the basis - the IRS generally accepts reasonable estimates when you can demonstrate good faith effort to determine the correct amount.