Does anyone know if you can apply NOL carryforwards when using tax software like TurboTax or do you need an accountant? I'm trying to save money since I'm still in startup mode but don't want to miss out on using my losses from last year.

Just want to add my experience as someone who went through this recently. I had about $8k in losses from my graphic design business startup costs and was able to carry them forward successfully. The key thing I learned is that you need to distinguish between startup costs (which might need to be amortized over 15 years) and regular business operating expenses (which can create the NOL immediately). Things like your office supplies, software subscriptions, and marketing expenses that you mentioned should qualify for immediate NOL treatment. But if you had any costs related to actually starting the business (like legal fees to set up your LLC, initial market research, etc.), those might fall under the startup cost rules and need different treatment. I'd recommend keeping track of which category each expense falls into - it'll make carrying forward much smoother and help if you ever get questioned about it. The NOL carryforward has been a lifesaver for offsetting my profits this year!

As someone who's been through this decision process myself, I can definitely relate to the audit anxiety! I used to pay for TurboTax Audit Defense every year until I realized I was basically paying for peace of mind rather than actual value. What helped me make the decision to skip it was doing some research on IRS audit statistics for my income bracket and tax situation. For most middle-income taxpayers with straightforward returns, the audit rate is incredibly low. I also looked at what the service actually covers - it's representation and communication with the IRS, but it doesn't cover any additional taxes, penalties, or interest you might owe if issues are found. I ended up canceling my Audit Defense and instead put that money into a high-yield savings account as my "tax emergency fund." Three years later, I haven't needed it, but if I ever do get audited, I'll have the money saved to hire a CPA who specializes in audit representation rather than paying premiums year after year for something I'm unlikely to ever use. The key is really good record-keeping. I keep digital copies of all my receipts, maintain detailed expense logs for any business deductions, and organize everything by tax year. If you're already doing that and your tax situation isn't super complex, you're probably better off saving the money and handling any potential issues if and when they arise.

I've been wrestling with this same decision for years! After reading through everyone's experiences here, I'm finally convinced to drop the Audit Defense for my 2025 return. What really sealed it for me was learning that the audit rate is less than 1% for most individual taxpayers, and hearing from people who actually used the service and found it pretty underwhelming. It sounds like you're mostly paying for someone to be a middleman between you and the IRS rather than getting actual advocacy. I think the fear-based marketing really gets to people (myself included). They make it sound like you'll be completely helpless if audited, but from what I'm reading here, good record-keeping and documentation are your best defense anyway. And if something does come up, you can always hire a CPA who actually specializes in audit representation at that point. I'm going to take the advice several people mentioned about putting that audit defense money into a dedicated savings account instead. At least that way I'm building up funds that I control, and if I ever do need professional help with the IRS, I'll have money saved specifically for that purpose. Much better than paying premiums year after year for something I'll statistically never need. Thanks to everyone who shared their real experiences - this discussion has been way more helpful than any TurboTax marketing material!

Something no one mentioned yet - make sure you and your spouse don't accidentally exceed the family limit COMBINED during the transition months. When my husband and I went through this, our benefits department counted wrong and we over-contributed by accident. Had to withdraw the excess contribution before filing taxes which was a hassle because we'd already spent some of the HSA funds on medical expenses. Just double check all your calculations!

This is such a timely question! I just went through something similar when my partner switched jobs mid-year. One thing that really helped me was keeping detailed records of exactly when each coverage period started and ended - down to the specific dates, not just months. The IRS can be pretty strict about the timing, especially if there are any gaps in coverage or overlapping periods. I'd recommend documenting everything: when your wife's current coverage under your plan ends, when her new employer's coverage begins, and whether there's any continuation coverage (like COBRA) in between. Also, don't forget about the catch-up contributions if either of you is 55 or older! Those rules can get even more complex with mid-year changes. The additional $1,000 catch-up contribution follows the same monthly calculation rules, so you'd need to factor that in too. One last tip - consider setting up automatic contributions to match your calculated monthly limits rather than trying to make one large contribution at year-end. It helps avoid accidentally over-contributing and makes the whole process much more manageable.

One more thing to keep in mind - if the cabin was inherited, you likely get a "stepped-up basis" which means your cost basis is the fair market value when you inherited it, not what your grandparents originally paid. This can significantly reduce your capital gains tax! For example, if your grandparents bought the cabin for $50,000 but it was worth $200,000 when you inherited it, your basis is $200,000. If you sell it for $250,000, you only pay capital gains on the $50,000 difference, not the full $200,000 gain from the original purchase price. Make sure you have documentation of the property's value at the time of inheritance (like an appraisal from the estate) since this will be crucial for calculating your actual taxable gain. This could save you thousands in taxes compared to what you might initially think you owe!

This is exactly the situation I was in a few years ago! One thing that really helped me was understanding the "safe harbor" rule - if you pay at least 100% of last year's tax liability (or 110% if your prior year AGI was over $150,000) through withholding and estimated payments, you won't face underpayment penalties even if you end up owing more when you file. So if your total tax last year was $8,000, as long as you pay at least $8,000 this year through your regular W2 withholding plus estimated payments for the property sale, you're protected from penalties. This takes a lot of the guesswork and stress out of estimating the exact amount. I'd also recommend keeping detailed records of your property's basis (what your grandparents paid plus any improvements) since you'll need that to calculate your actual gain. Don't forget about selling expenses like realtor commissions, legal fees, and closing costs - these can be deducted from your gain and reduce your tax bill.

As someone who's dealt with similar year-end gift timing questions, I can confirm what others have said about the "unconditional delivery" rule. The IRS is actually quite reasonable about holiday banking delays - they understand that checks given in late December often can't be deposited until after New Year's due to bank closures and holiday schedules. Your situation is textbook for how gift timing works. Since you physically handed your niece the check in 2024, had sufficient funds available, and placed no restrictions on when she could cash it, the gift is complete for 2024 tax purposes regardless of when she actually deposits it in January. I'd suggest keeping a simple note in your records mentioning that the deposit delay was due to holiday bank closures - not required, but it provides helpful context if the timing ever comes up in the future. The most important thing is that you have documentation showing when you actually gave her the check, which it sounds like you do. You're well within the bounds of what the IRS considers "reasonable time" for cashing a gift check, so you should be all set to count this toward your 2024 annual exclusion limit!

This has been such a comprehensive discussion! As someone who's made similar year-end gifts before, I can confirm that your $17,000 check definitely counts toward your 2024 exclusion since you delivered it with adequate funds and no restrictions. One thing I haven't seen mentioned yet is that you might want to give your niece a heads up about the timing if she's not already aware. Sometimes recipients don't realize that holding onto gift checks for too long could potentially create complications, even though a few weeks is totally fine. Just a simple "hey, when you get a chance to deposit that check in January, that would be great" text can help ensure everything goes smoothly. Also, this situation is actually a perfect example of why some people prefer making electronic transfers for large gifts - no worries about banking hours or check-clearing delays. Though obviously that requires the recipient to be set up for electronic transfers, which isn't always practical for every situation. You handled this exactly right, and the documentation suggestions from others in this thread are spot-on for future reference!