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I'd like to add one more important piece to this HSA discussion - even though you can't contribute to an HSA while on a PPO, you might want to look into a Flexible Spending Account (FSA) if your wife's employer offers one. FSAs also allow pre-tax contributions for medical expenses, though they typically have a use-it-or-lose-it policy at year end. Then when you do switch to the HDHP in 2025, you can start funding the HSA. Just remember you generally can't have both an FSA and HSA simultaneously unless the FSA is a "limited purpose" one that only covers dental and vision expenses.
I actually hadn't thought about the FSA option! Does it provide the same tax advantages as an HSA? And what happens to any FSA funds when we transition to the HDHP with an HSA in 2025?
FSAs do provide a similar tax advantage by allowing pre-tax contributions that reduce your AGI, similar to an HSA. However, they typically have much lower contribution limits (usually around $3,050 for 2023) compared to HSA limits ($7,750 for family coverage). Regarding your second question, FSA funds generally need to be used by the end of your plan year, though some employers offer either a grace period (usually 2.5 months) or a carryover option (usually $610 maximum). If you don't use the funds within these timeframes, you forfeit them - that's the big downside compared to HSAs. When you transition to an HDHP with HSA in 2025, you'll need to either spend down your FSA funds before the new plan year or see if your employer offers that limited purpose FSA I mentioned that can coexist with an HSA.
One thing to consider that nobody's mentioned - if your wife's employer offers an HSA-eligible plan NOW, you might be able to switch to it mid-year if you have a qualifying life event (like marriage, birth, loss of other coverage). You don't always have to wait for open enrollment. If you can switch to an HDHP sooner, you could start making prorated HSA contributions for the months you're eligible this year.
This is great advice! When I had my second child last year it counted as a qualifying life event and I was able to switch from a PPO to an HDHP mid-year. Started contributing to my HSA right away for the remaining months.
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Don't forget to check if your state has any additional deductions for home purchases! Federal and state taxes treat some closing costs differently. In my state, we get an additional deduction for certain recording fees that aren't deductible federally. Also, keep your closing documents forever! You'll need them when you eventually sell the house to calculate your basis and potential capital gains.
Do mortgage points get deducted all at once in the year you buy, or do they have to be spread out over the life of the loan? I've heard conflicting info.
Points can be tricky. For your main home, if the points meet certain IRS criteria, you can deduct them fully in the year you paid them. Otherwise, you have to spread the deduction over the life of the loan. To deduct them all at once, the points need to be for your primary residence, be a standard practice in your area, not be excessive, and a few other requirements. If it's a refinance rather than a purchase, you typically have to amortize the points over the loan term.
freetaxusa actually has a pretty decent help section if you search for "home purchase." That's how I found where to enter my stuff. It's definitely not as obvious as it should be! The standard deduction is so high now that unless you have a really expensive home with high property taxes and mortgage interest, or lots of other itemizable deductions, you might end up taking the standard deduction anyway.
I always get confused about whether I should itemize or take the standard deduction. Is there an easy way to know which is better without doing all the work to itemize first?
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In my experience, TurboTax is pretty comprehensive but it doesn't always ask the right questions for complex situations. Last year I switched to a CPA and he saved me about $3,800 compared to what TurboTax calculated. The biggest areas where I found savings: - Business expense deductions I didn't realize qualified - More advantageous treatment of some investment losses - Home office deduction I didn't know I was eligible for For your situation with S-corp income, a good tax pro might find some legitimate business expenses you could deduct. They also might have strategies around timing of income recognition or loss harvesting that could help reduce your tax bill.
How much did the CPA charge? I'm trying to figure out if the cost would be worth it compared to potential savings.
My CPA charged $450 for my return, which included W-2 income, investment income, and some small business income from consulting. Given that he saved me $3,800, it was definitely worth it! Most CPAs I researched charged between $350-700 for returns with complexity similar to yours. The key is finding someone who specializes in the areas relevant to your situation - in your case, someone experienced with S-corporations and investment income.
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Speaking from experience as someone who's been through almost the exact same situation (gifting to unmarried partner who did contracted work for my business), make sure you have a FORMAL, written contract for her work responsibilities. Back-date nothing. Pay her consistently, not in lump sums that could be confused with the gift. Also, consider speaking with an estate planning attorney, not just a CPA. My attorney suggested structuring part of this as a trust for your children rather than a direct gift to your partner, which can have additional benefits beyond just the immediate tax situation.
Can you explain more about the trust option? Wouldn't that defeat the purpose of giving the girlfriend financial independence if the money is tied up in a trust for the kids?
You're right that a trust solely for the children wouldn't address the goal of financial independence for the girlfriend. What my attorney suggested (and what we ended up doing) was a combination approach: a direct gift to my partner for her immediate financial security, plus a separate family trust where she was both a beneficiary and a trustee. This had several advantages: it reduced the immediate gift tax implications by splitting the amounts, it provided structured financial security for both her and our children, and it created an additional layer of documentation showing the personal nature of these financial arrangements. The trust paperwork explicitly referenced our family relationship, which further reinforced that these were personal financial planning decisions rather than business compensation.
Has anyone considered whether there might actually be a benefit to structuring some of this as increased compensation instead of a gift? If your business is profitable, wouldn't it be better to take the business deduction on at least part of this amount? Maybe increase her contracting rate or give her a significant bonus for a special project?
Bad idea. The IRS would absolutely flag that as suspicious. Going from $50K to suddenly hundreds of thousands in "contractor fees" would trigger an audit instantly. Plus, even if it was legitimate, she'd have to pay self-employment tax on all of that, which is around 15%. That's a huge tax hit compared to receiving it as a gift.
Ravi Kapoor
Just so you know, if your income was only $2,800 for the year, you're almost certainly not required to file. But as others have mentioned, you might be leaving money on the table by not filing. One thing nobody has mentioned: if you're expecting to receive disability backpay, be aware that could create a tax situation in the year you receive it. If you get approved and receive a large lump sum, you might want to look into something called "lump sum election" which can help reduce the tax impact by allocating the income to previous years. Also, regarding the survey sites not sending 1099s - that's normal if each one paid you less than $600. But you're still required to report that income. The good news is you can also deduct any expenses related to earning that income, like a portion of your internet bill.
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Amina Toure
•Thanks, that's really helpful about the lump sum election. I hadn't even thought about the tax implications of getting disability backpay. Do you know if I would need to file amended returns for the previous years in that case, or is it handled differently?
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Ravi Kapoor
•You don't need to file amended returns for the previous years with a lump sum election. Instead, when you file your taxes for the year you receive the backpay, there's a special calculation that's done on that year's return. The SSA will send you a letter (SSA-1099) showing how much of your payment applies to each previous year. Your tax preparer (or tax software) can then use this information to calculate your tax as if the income had been received in those earlier years, potentially putting you in a lower tax bracket for the lump sum. It's a bit complex, but any tax professional familiar with disability claims should know how to handle it. And definitely keep all documentation about your medical expenses, as some of those might be deductible as well.
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Freya Nielsen
I don't mean to be that person, but I think you should know that the IRS can come after you years later if you don't file. My cousin didn't file for 3 years when he was making very little money, and they eventually sent him notices with penalties and interest. Even if you don't owe anything now, I personally wouldn't risk it. Look into the free filing options others have mentioned. The VITA program helped my grandmother last year and they were actually very professional. They're often accounting students or retired CPAs volunteering their time. Also, check if your state has any specific low-income credits you might qualify for. Some states have additional credits beyond the federal ones that are specifically for people in situations like yours.
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Omar Mahmoud
•I second the VITA suggestion. I used them when I was in college and they were great. Just make sure to bring all your documentation - they'll want to see your ID and social security card, plus any income info you have (even if it's just printouts from the survey sites showing your earnings).
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