That's a great suggestion I hadn't thought of! Do you know if these built-in calculators typically handle all the different pre-tax options and show the tax implications clearly? Our HR system is ADP but I haven't fully explored all its features.

Most employer HR systems with these calculators do handle all the pre-tax options specific to your company's benefits package. They're usually more accurate than generic calculators because they're configured with your exact benefit structure. ADP definitely has this feature! Look for something called "Paycheck Modeling" or "Net Pay Calculator" in your ADP portal. It should let you adjust all available pre-tax deductions and show exactly how they affect your take-home pay. If you can't find it, ask your HR department - sometimes these features aren't enabled by default.

I use the TurboTax tool every year after doing my taxes. It's decent but doesn't really show the impact of changing pre-tax deductions in real-time. It's more focused on getting your W-4 withholding right than optimizing across different pre-tax options. I ended up using a combination of that plus a separate calculator for my 401k/HSA decisions.

Thanks for the feedback! You're right that it's more withholding-focused. I just found it useful as one piece of the optimization puzzle. I've been looking for something more comprehensive that shows the trade-offs between different pre-tax options in real-time.

How do we handle the expenses for equipment and software? We've been sharing the costs pretty informally. Do we need to track every single purchase?

You absolutely need to track every single purchase related to your YouTube work. Keep all receipts (digital or physical) and note which partner paid for what. The partnership should track all these expenses, even if they came from personal funds. For equipment and software, these are legitimate business expenses that can offset your income. Just make sure you're only deducting the business portion (if you also use things personally). You'll need to decide if certain equipment should be depreciated over time rather than expensed immediately - this depends on cost and expected useful life.

That's actually tax fraud and could get both of them in serious trouble. The IRS isn't stupid - they know people try these "creative" approaches. What you're describing is trying to avoid paying self-employment taxes and income taxes by mischaracterizing business income as gifts. The company clearly views them as a single business entity, which is why they're asking for one W-9. The proper way to handle this is exactly what the top comments suggest - file as a partnership, get an EIN, and each partner reports their share of income on their personal returns.

Can CPAs help with issues from prior year returns? I think I messed up my 1099-MISC reporting for a rental in 2023 and I'm worried about an audit.

Yes, CPAs can absolutely help with prior year issues. They can prepare amended returns (Form 1040-X) to correct mistakes from previous filings. For your 1099-MISC situation, they could review what you submitted and determine if an amendment is necessary. Many CPAs also offer audit representation if the IRS does question your return. Having someone who understands the tax code represent you during an audit can be extremely valuable, especially for rental property issues which tend to be scrutinized more closely.

I thought moving expenses weren't deductible anymore after the tax law changes? Was this for a military move or something special?

Thank you for mentioning state taxes! I completely forgot about that aspect. Do you know if most states follow the same $400 self-employment threshold as federal, or does it vary a lot by state?

State tax requirements vary quite a bit. Some states like Florida, Texas, and Nevada don't have any income tax at all, so you wouldn't need to file a state return there. Other states have their own thresholds that might be different from the federal $400 self-employment threshold. For example, California requires filing if you have any income tax withheld or if your income exceeds certain thresholds based on filing status and age. Some states also have special rules for self-employment income specifically.

This is so important! When I first started freelancing, I didn't track expenses properly and ended up paying way more in self-employment tax than I needed to. Now I keep receipts for everything business-related.

Do you know which other states besides California might still allow these deductions? I'm in New York and wondering if I might be able to at least get some benefit on my state return.

New York does still allow miscellaneous itemized deductions subject to the 2% floor, including unreimbursed employee business expenses! So while you can't take these deductions on your federal return, you can still claim them on your New York state return. Minnesota and Arkansas also didn't fully conform to the TCJA changes regarding these deductions. Several other states have their own versions of itemized deductions that might help, but the rules vary significantly. Just make sure you're keeping detailed records - date, starting location, ending location, mileage, and business purpose for each trip.

I appreciate this suggestion! Do you happen to know if there are any red flags this might raise with the IRS? And roughly what percentage of my work would need to fall under the S-Corp for this to make sense financially?

This approach definitely needs careful consideration as the IRS does scrutinize arrangements where someone works as both an employee and contractor for related entities. The work performed under each arrangement must be legitimately different to justify the separate classification. Generally, CPAs recommend at least 15-20% of your total income should come through the S-Corp for the setup and maintenance costs to make sense. Remember there are additional expenses with an S-Corp including separate accounting, potentially additional insurance, and compliance requirements. The miles between locations would only be deductible for travel related to your S-Corp work, not your W2 employment.