Pay nothing until a live IRS agent is on the phone with you.
Can't reach IRS? Claimyr calls for you, so you don't have to wait on hold.
$0 upfront. We only hold your card.
No live agent, no charge.
$9.99 is charged only once a live IRS agent is on the phone with you.
Using Claimyr will:
- Connect you to a human agent at the IRS
- Skip the long phone menu
- Call the correct department
- Redial until on hold
- Forward a call to your phone with reduced hold time
- Give you free callbacks if the IRS drops your call
Ask the community...
- DO post questions about your issues.
- DO answer questions and support each other.
- DO post tips & tricks to help folks.
- DO NOT post call problems here - there is a support tab at the top for that :)
Join the conversation
Join the conversation
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.
Join the conversation
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.
Join the conversation
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.
Join the conversation
I completed a cross-state 1031 last year (CA to TX) and the one thing nobody mentioned yet is state tax implications. Since you're going from AZ to IN, you should check if Arizona tries to tax the deferred gain when property leaves the state. Some states have "clawback" provisions. In my case, California wanted their piece of the pie even though I moved to Texas. Had to file a special form with CA acknowledging the deferred gain. Don't know about AZ specifically, but worth checking into before you complete the exchange.
That's a really good point I hadn't considered. Do you know if there's any resource specifically about Arizona's policies on this? I definitely want to avoid surprise tax bills from AZ after I've moved to Indiana.
I don't know Arizona's specific rules, but I'd recommend calling the Arizona Department of Revenue directly. That's what I did with California. For what it's worth, most states follow the federal treatment and don't try to tax the gain immediately, but some have started implementing these clawback provisions to prevent losing tax revenue when property owners leave the state. Usually there's a form you need to file acknowledging the deferred gain and agreeing to file nonresident returns if you later sell the replacement property.
One thing to be careful about with cross-state 1031 exchanges is making sure you're working with a qualified intermediary who is licensed in both states. I learned this the hard way.
Is that really a thing? I thought QIs weren't actually licensed in most states. They're not like real estate agents with state-specific licenses. At least that's what I understood.
Raj Gupta
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.
0 coins
Lena Müller
•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.
0 coins
Raj Gupta
•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.
0 coins
TechNinja
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.
0 coins
Keisha Thompson
•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?
0 coins