Just a heads up - if your kids are under 18 and it's a sole proprietorship, having them as W-2 employees can save you both from paying Social Security and Medicare taxes on their wages. That's a 15.3% savings right there! My accountant saved me a ton by setting this up correctly last year.

One thing I haven't seen mentioned yet is documentation. Regardless of whether you go the W-2 or 1099 route, make sure you keep detailed records of the work your kids performed, hours worked (if applicable), and how you determined their pay. For seasonal work like yours, document what specific tasks they did - was it general labor following your direction, or more specialized independent work? Did they work set hours you assigned, or flexible schedules they controlled? These details matter a lot for proper classification. Also, consider having them fill out timesheets or work logs, even if they end up as contractors. It shows you're taking the classification seriously and helps protect you if there are ever questions. The IRS loves good documentation, especially with family business arrangements where they're naturally more suspicious. Since you mentioned this is your first time doing this, it might be worth consulting with a local tax professional who can look at your specific business structure and work arrangements. The potential penalties for misclassification often cost more than getting proper advice upfront.

I've been self-employed for about 5 years now, and I've tried almost all the tax software options. Here's my two cents: TurboTax Self-Employed is good but expensive. It does handle Schedule C well and provides good guidance, but you're paying a premium for the brand name. H&R Block Self-Employed is similar in quality and price to TurboTax. TaxAct and TaxSlayer both handle Schedule C for significantly less money. FreeTaxUSA is my personal favorite - it handles Schedule C perfectly well, the interface is clean, and it's WAY cheaper than TurboTax. If your situation is truly simple as you describe (just income, standard deduction, QBI, and SE tax), any of these will work fine. The difference mainly comes down to how much guidance you want and how much you're willing to pay for it.

One thing no one mentioned yet - if your self-employment income is below a certain threshold (I believe it's around $73,000 for 2024), you can use the IRS Free File program to file for free, including Schedule C. Different companies participate in this program, including some versions of TurboTax, TaxSlayer, etc. Just go through the IRS Free File portal rather than directly to the tax software websites, otherwise they'll try to upsell you. This is different from the "free" versions advertised on their websites, which typically don't support Schedule C filing.

If you filed with a professional tax preparer last year, they might have your PIN or a copy of your return with the AGI on file. Worth giving them a call if that's how you filed. I completely forgot I had used H&R Block last year until I started panicking about my PIN, gave them a call, and they had everything I needed.

Another option if you're still stuck is to request an Identity Protection PIN (IP PIN) from the IRS if you qualify. This is different from your self-select PIN and can be used for identity verification when e-filing. You can check if you're eligible on the IRS website - they've expanded the program in recent years. Also, just a heads up that if you do end up creating a new self-select PIN this year, consider storing it in a password manager or writing it down somewhere safe along with your AGI. I learned this lesson the hard way after going through the same frustration you're experiencing! The IRS recommends keeping your prior year tax return easily accessible for exactly this reason.

Has anyone used specific tax software that handles ESPP sales and wash rules correctly? I tried TurboTax last year and it completely messed up my ESPP reporting.

Great thread - this is exactly the kind of ESPP situation that trips people up! Just want to add one important point that hasn't been fully addressed: when you left your job in March, your company likely processed what's called an "accelerated vesting" for your ESPP shares, which is why they all became available to sell even if they hadn't met the normal holding periods. This is pretty standard when employment ends. The key thing to remember is that since you're no longer employed there, you won't have any future ESPP purchases that could trigger wash sales. Your main concern should be any RSU vestings or option exercises you might still have scheduled, or if you're planning to buy the stock on the open market. Also, make sure you get your final W-2 from your former employer - they should report any ESPP discount as ordinary income if you end up making disqualifying dispositions, and you'll need that for accurate tax reporting.

One thing to keep in mind - even if your return doesn't show up in the system yet, you can still make a payment toward what you owe to stop additional penalties and interest from accruing. Go to IRS Direct Pay and choose "extension payment" as the reason. The payment will be applied to your account regardless of whether your return is fully processed yet. You can then set up the formal payment plan once everything is visible in the system.

The maintenance periods are super annoying! I filed right before one last year too. Just FYI, you might want to check the status of your return using the "Where's My Refund" tool even though you owe money. Sometimes it will show processing status even when your account doesn't show it yet.