I've been trading for about 6 years and went through the same analysis paralysis you describe. Here's what I learned the hard way: The S-Corp route can work, but you need to factor in the additional costs beyond just filing fees. You'll need quarterly payroll processing, workers' comp insurance (even as the sole employee), and potentially state franchise taxes. In my case, these costs ate into the self-employment tax savings significantly. One thing that helped me was tracking my trading patterns for a full year before making any MTM decisions. I kept a simple log of when I had open positions at year-end vs when I closed everything out. Turns out I naturally close most positions before December anyway, which made MTM less beneficial since I wasn't carrying many paper gains/losses into the new year. For wash sales, I'd recommend being extra careful with December trading. Even though the loss isn't permanently gone, having it deferred to the next tax year can mess up your quarterly estimated payments if you're not expecting it. I got hit with underpayment penalties one year because of this timing issue. The broker tracking issue others mentioned is real - I use three different platforms and have to manually reconcile everything. It's tedious but necessary if you want accurate reporting.

Great discussion everyone! As someone who's been through similar analysis, I want to add a perspective on the psychological aspect of these tax strategies that often gets overlooked. I spent two years obsessing over MTM election and S-Corp structures, running endless scenarios and calculations. What I realized is that the mental bandwidth consumed by complex tax strategies was actually hurting my trading performance. The cognitive load of tracking wash sales across multiple accounts, worrying about year-end positions for MTM, and managing corporate paperwork was distracting me from what actually generates profits - good trading decisions. Sometimes the "suboptimal" tax approach that's simple and automated is actually optimal when you factor in the time and mental energy costs. My trading improved significantly when I simplified to a single broker with good tax reporting and accepted that I might pay a bit more in taxes but gained back focus and trading clarity. That said, for high-volume traders with substantial profits, the complexity can definitely be worth it. The key is being honest about whether the tax savings justify the operational overhead for your specific situation and trading style.

I completely understand your frustration with this contractor - it's maddening when someone tries to weaponize tax documents over a business dispute. The good news is you're in a much better position than you might think. Since you kept everything organized in that separate account, you have exactly what the IRS needs. Even with the account closed, call your bank's customer service and explain you need statements for tax purposes - they're required to provide records from closed accounts for several years. Most banks will email or mail these to you within a few business days. Here's what I'd do: First, send one final certified mail request for the 1099-NEC with a 10-day deadline - this creates an official paper trail. Then gather every piece of documentation you have (bank statements, invoices, emails about payments). Calculate your exact income from these records and file using Schedule C for self-employment income. The IRS deals with situations like this constantly. They actually have procedures specifically for when contractors refuse to provide required forms. Your three dependents and substantial refund shouldn't be held up by someone who's clearly being vindictive. File based on your records - the IRS is far more concerned with people who don't report income at all than with good-faith efforts to report accurate amounts when contractors don't cooperate. Don't let this person control your tax timeline any longer. You've done everything right by keeping organized records.

I've been following this thread and wanted to add something that might help - you should also consider filing Form SS-8 with the IRS to request an official determination of your worker classification. Given what you've described about the payment dispute and your former employer's controlling behavior, there's a good chance you were misclassified as an independent contractor when you should have been treated as an employee. If the IRS determines you were actually an employee, you'd be entitled to file Form 8919 to recover the employer portion of Social Security and Medicare taxes, which could save you around $1,000 on that $13,000 in earnings. This is separate from your immediate need to file your return, but it's worth pursuing given the circumstances. The fact that he tried to dictate what he thought was "fair" payment rather than honoring your agreement is a red flag for employee relationship. Independent contractors typically have more control over their compensation and working arrangements. Even if this doesn't help with your current filing situation, it could result in significant tax savings down the road. Don't let his vindictive behavior cost you money you're rightfully owed. File your return based on your records as others have suggested, but definitely look into the worker classification issue as well.

To all those having trouble reaching a human at the IRS. I just ran across this video that gave me a shortcut to reach a human. Hope it helps! https://youtu.be/wMf29SmRU-I

Yes, you should still get your refund on 3/2/2021! The 846 code shows your federal refund issue date, and the 898 code is just showing the state tax offset that will be deducted from your total refund amount. The IRS will send you whatever's left after the offset on the 846 date. So if your original refund was $5000 and the state offset is $1000, you'd get $4000 on 3/2. The different dates just show when each action is processed in their system, but your net refund should still come on the 846 date.

unpopular opinion but H&R Block's interface is actually better than TurboTax now ngl

Been using TaxAct for the past 3 years and honestly it's been solid. Way cheaper than TurboTax (like $25 vs $120+) and I've never had issues with accuracy. The interface isn't as flashy but it gets the job done. Also has good customer support if you get stuck on something. Might be worth adding to your comparison list!

Another helpful resource that I don't think has been mentioned is your state's tax website. Many states have specific guidance about Box 14 items that might be deductible or require special handling on your state return, even if they don't affect your federal taxes. For example, some states allow deductions for union dues, professional association fees, or certain insurance premiums that employers report in Box 14. Others have specific rules about how to handle transit benefits or parking allowances. I discovered this when I was confused about a "STD" code in my Box 14 (which turned out to be state disability insurance). My state's tax website had a whole section explaining how to handle these premiums as a potential itemized deduction. Would have never found this information just looking at federal tax resources. Your state's Department of Revenue or Treasury website usually has these guides in their individual taxpayer sections. Worth checking even if you think your Box 14 items are just informational!

I've been following this thread and wanted to share one more approach that helped me with mysterious Box 14 codes - checking your employee benefits enrollment confirmation or summary from when you signed up for benefits at the beginning of the year (or when you were hired). Many employers send out a benefits confirmation that lists exactly what you enrolled in and the payroll codes associated with each benefit. I found mine in my email from last January and it had a table showing things like "Code: HLTH - Health Insurance Premium Share" and "Code: FSA - Flexible Spending Account Contribution." This was way more helpful than trying to decode abbreviations after the fact. It also reminded me of benefits I had completely forgotten about, like the legal services plan I signed up for that was showing as a weird three-letter code in Box 14. If you can't find your benefits confirmation email, many companies also include this information in their employee handbook or benefits guide, which might be available on your company intranet or through HR. Sometimes they even have a glossary of payroll codes in the back of these documents!