Has anyone actually looked at OP's investment options with Paylocity? Are they mainly target date funds or do they have some decent index fund options? The fees make a huge difference over time.

Great decision Tyler! You've got a solid plan there. Just wanted to add a few practical tips for when you start doing those transfers: 1. Keep track of your transfer dates - most HSA providers limit you to 1-2 free transfers per year, so you'll want to batch them up rather than doing frequent small transfers. 2. Consider doing your first transfer once you hit around $2,000-3,000 in your Paylocity account. This way you're past their minimum balance requirement and have a decent amount to make the transfer worthwhile. 3. When you do transfer, leave a small buffer in your Paylocity account (maybe $100-200) to cover any potential fees or timing issues with future payroll contributions. 4. Make sure to update your investment allocations in both accounts so new money gets invested automatically rather than sitting in cash. The fee difference you mentioned (0.35% vs Fidelity's zero-fee funds) will really add up over time. On a $10,000 balance, that's $35/year you're saving, and as your HSA grows to $50,000+ over the years, you'll be saving hundreds annually. Smart move!

idk why but this whole thing of kids getting 1099s is wild to me. back in my day we just had lemonade stands 👴

Just to add some clarity here - yes your child can absolutely receive a 1099 at any age! Since they made $600 from content creation, whoever paid them should issue a 1099-NEC if it was from a single source. The key things to remember: 1) They'll need to file their own return since it's self-employment income over $400, 2) You can still claim them as your dependent, and 3) Definitely set aside money for taxes (self-employment tax is 15.3% plus regular income tax). Also make sure to track all business expenses - equipment, internet costs, etc. can be deducted!

This is such a common issue! I went through the exact same thing my first year freelancing. Your CPA's advice is spot on - you only need to report actual business income, not personal transfers from family and friends. Here's what helped me get organized: I exported all my Cash App transactions to a spreadsheet and created columns for "Business Income," "Business Expense," and "Personal." Then I went through line by line and categorized everything. It was tedious but gave me peace of mind. The key things to remember: - Gifts from family/friends are NOT taxable income to you - Money for splitting bills, rent help, etc. are personal transfers, not income - Only payments for goods/services you provided count as business income - Keep notes explaining each transaction in case of questions later You're already doing the right thing by separating accounts going forward. For this year's filing, just be thorough with your categorization and keep good records. The IRS understands that people use these apps for both personal and business - they just want to see that you're reporting your actual business income correctly.

I went through this exact same situation last year and wanted to share what worked for me. The mixed personal/business transactions in Cash App were giving me major anxiety, but it turned out to be much more manageable than I thought. Here's my step-by-step approach that might help: 1. Export your entire Cash App transaction history to CSV 2. Create a simple spreadsheet with columns for Date, Amount, Description, and Category 3. Go through each transaction and mark it as either "Business Income," "Business Expense," or "Personal" 4. For business transactions, add a note about what service/product was provided 5. Calculate your total business income and expenses separately The personal stuff (family gifts, splitting dinner bills, rent help) doesn't affect your taxes at all - the IRS only cares about money you earned through business activities. Your CPA was right that it's straightforward, but I totally understand the stress of making sure you get it right. One thing that helped me was printing out the final categorized list and highlighting all the business income entries. Having it on paper made it feel more official when I handed it to my accountant. Also, keep all those records! I put everything in a folder labeled "2023 Tax Backup" just in case. The peace of mind is worth it. You've got this - the hardest part is just sitting down and going through everything methodically.

Use TurboTax or FreeTaxUSA - they make it super easy to enter even tiny W-2s like this. Takes maybe 2 minutes and saves all the worry. I had a similar situation with a $45 W-2 last year and just entered it to avoid any headaches.

Just to add another perspective - I work in payroll and can confirm that employers are required to issue W-2s for any amount of wages paid, even if it's just $24.50. The lack of federal tax withholding is completely normal for such a small amount - the withholding tables are designed so that very low earnings don't trigger federal income tax withholding. However, as others have mentioned, you absolutely should report this income. The IRS receives copies of all W-2s electronically, and their automated matching system will flag your return if there's a discrepancy. Even though the actual tax impact might be zero (depending on your total income), omitting it could trigger correspondence that's way more hassle than just including it. Pro tip: If you're using tax software, it will automatically calculate whether this small amount actually affects your tax liability. In many cases, it won't change what you owe or your refund amount, but reporting it keeps you compliant and avoids potential issues down the road.

Has anyone dealt with a situation where you owned a house together during the divorce process? We're selling our house as part of the divorce but it won't close until after we file taxes. Not sure how to handle this on my return if I file separately.

Just wanted to add another important consideration that hasn't been mentioned - if you're receiving any kind of spousal support or alimony payments during the separation, this can significantly impact which filing status makes the most sense financially. If you're the one paying support, you can deduct those payments when filing separately (but not if you file jointly). If you're receiving support, you'll need to report it as income regardless of filing status. This could push you into a higher tax bracket or affect your eligibility for certain credits. Also, don't forget about state taxes! Some states have different rules than federal, so even if you're required to file as Married Filing Separately for federal taxes, your state might have different options available. Worth checking with a local tax professional who knows your state's specific rules.