What about cash expenses for business? I sometimes pay day laborers in cash for help with my landscaping business - how do I prove these are legitimate?

Great thread! As someone who went through my first business tax filing this year, I learned the hard way that organization is EVERYTHING. The IRS basically expects you to be able to prove every single deduction you claim. One thing that really helped me was setting up a simple system from day one: I use a dedicated business checking account, immediately photograph receipts with my phone, and keep a simple spreadsheet noting the business purpose of each expense. Even small purchases like office supplies get documented. The key insight I had is that the IRS isn't necessarily looking to catch you doing something wrong - they just want to see that you're being reasonable and keeping proper records. If you can show clear business purpose and have documentation to back it up, you're usually fine. For anyone just starting out like the original poster, my advice is to err on the side of over-documenting rather than under-documenting. It's way easier to establish good habits from the beginning than to try to reconstruct everything later if you get audited.

Anyone know if these ticket sales count toward the threshold where you need to make estimated tax payments? I normally just get a W-2 but sold about $8k in tickets last year and made like $1500 profit.

For anyone still confused about this, I just want to clarify the key points since there's some conflicting advice in this thread: 1. You MUST report the full 1099-K amount as gross income - don't just report the net profit like one commenter suggested. The IRS computer systems automatically match 1099-K forms to tax returns, and reporting only the net will trigger a notice. 2. Whether you use Schedule C or Schedule 1 depends on your intent and frequency. If you bought tickets specifically to resell for profit or do this regularly, it's a business (Schedule C). If you're just selling tickets you can't use occasionally, it's hobby income (Schedule 1, Line 8i). 3. You can deduct BOTH your original ticket costs AND the platform fees. The 1099-K shows gross payments before StubHub's fees were deducted, so you're not double-counting anything. 4. Keep good records! Save your original purchase confirmations, credit card statements, and any communications about the sales. The IRS may ask for documentation. The software tools mentioned here (taxr.ai) seem helpful for organizing everything, but make sure you understand the fundamentals so you can verify the results make sense.

Congratulations on the pregnancy! You're absolutely right that you can update your W4 in January for a baby expected in June. The IRS looks at your tax situation as of December 31st, so as long as your child is born in 2025, you'll qualify for the full child tax credit. One thing I'd suggest is using the IRS W4 calculator on their website to help you figure out the exact adjustment. It's free and walks you through all the scenarios. Just make sure to account for any unpaid parental leave you might take - that reduced income could affect your overall tax situation. Also, don't forget you'll need to get a Social Security number for your baby pretty quickly after birth to claim them on your taxes. The hospital usually provides the paperwork, but it can take a few weeks to process. Good luck with everything!

This is great advice everyone has shared! I'm in a similar boat - expecting in August and trying to optimize our withholding. One thing I'd add from my research is to also consider if either parent's employer offers dependent care FSA (flexible spending account) benefits. You can typically elect this during open enrollment or after a qualifying life event like having a baby. If you're planning to use childcare after your parental leave, you can set aside up to $5,000 pre-tax annually for dependent care expenses. This won't affect your W4 directly, but it's another way to reduce your overall tax burden for the year. Also, for those mentioning unpaid leave - some states have paid family leave programs that might affect your income calculations differently than unpaid FMLA. Worth checking what your state offers since that could impact how much you want to adjust your withholding. Henry, sounds like you've got a solid plan! Just make sure to revisit your withholding after the baby arrives and you have a better sense of your actual childcare costs and any other changes to your financial situation.

Just wanted to chime in as someone who went through a very similar situation last year. We had foundation issues discovered during inspection that cost us $22k to fix, and the buyer also backed out afterward. Like you, we were worried about timing and whether we could still count it toward our basis since it took several months to find another buyer. The good news is that everyone here is absolutely right - there's no 90-day rule for this type of situation. The IRS considers the timing to be when you owned the property and when the work was completed, not when you actually close on the sale. We ended up being able to add the full foundation repair cost to our basis even though it was 5 months between the repair and our eventual closing. One thing that really helped us was organizing all the documentation chronologically - the inspection report, estimates, invoices, proof of payment, and even correspondence with contractors. Our tax preparer said having everything well-documented made it much easier to justify the basis adjustment. Mold remediation definitely qualifies as a capital improvement since it addresses a health/safety issue and adds value to the property. Keep all those receipts - that $27k isn't lost money from a tax perspective!

This thread has been incredibly helpful! As a tax professional, I want to emphasize a few key points that have been correctly identified here: 1. There is absolutely no "90-day rule" for capital improvements when selling your primary residence. That timing restriction simply doesn't exist in the tax code for this situation. 2. Your $27k mold remediation is definitely a capital improvement that gets added to your home's basis, regardless of the 4-month gap between the work and closing. The IRS cares that you owned the property when the work was done and that it was completed before the sale - not about the specific timing between completion and closing. 3. Since this was remediation work identified through an inspection (health/safety issue), it clearly qualifies as adding value and extending the useful life of the property, which are the hallmarks of a capital improvement versus a repair. 4. With your primary residence exclusion ($500k for married filing jointly), you're likely in great shape tax-wise anyway, but having that $27k properly documented in your basis is still valuable. The most important thing now is keeping all that documentation organized - inspection report, estimates, invoices, proof of payment. You handled a difficult situation well, and from a tax perspective, everything is straightforward. That expensive mold remediation wasn't just money down the drain!

Don't forget to keep copies of EVERYTHING and proof of mailing! I made the mistake of not keeping good records when I mailed multiple returns last year. The IRS lost one of my returns, and I had to resend it. Now I scan all returns before mailing and get a certificate of mailing from the post office for each envelope (cheaper than certified mail but still gives you proof).

Adding to what everyone else has said about mailing separately - I work as a tax preparer and can confirm that separate envelopes is definitely the way to go. The IRS processing centers have different workflows for different tax years, and mixing them up can cause delays. One thing I haven't seen mentioned yet is to make sure you're using the correct mailing address for each tax year. The IRS sometimes changes processing center addresses between years, so double-check the instructions for 2022 vs 2023 returns. Also, if you owe money on both years, consider which one to prioritize if you can't pay both at once - generally you want to pay the older year first since penalties and interest accumulate longer on those. Good luck getting caught up! Don't stress too much - the IRS deals with late returns all the time.