Don't forget about the Qualified Business Income Deduction (Section 199A) which can give you a deduction of up to 20% of your qualified business income! This is separate from your business expenses on Schedule C and can really help reduce your tax bill as a 1099 worker. Also, make sure you're tracking and deducting your self-employment tax payments. You can deduct 50% of your self-employment tax on your 1040, which helps offset some of the extra tax burden from being self-employed.

You might also want to look into setting up a SEP IRA or Solo 401(k) for retirement. As a 1099 contractor, you're eligible for these self-employed retirement accounts which let you put away WAY more than regular IRAs. This won't help with last year's taxes, but could significantly reduce your tax bill going forward. With a Solo 401(k), you can contribute up to $22,500 as an "employee" for 2023 PLUS an additional 25% of your net self-employment earnings as the "employer" (up to combined limits). These contributions are tax-deductible and reduce your taxable income.

Based on my experience and what I've seen here, "Investor" is definitely the safest and most accurate choice for your situation. Since you're trading securities to generate capital gains (not running a business or providing services), that's exactly what an investor does - even if you're doing it actively. The key thing is that your occupation should match how you're actually filing your taxes. Since you don't qualify for trader tax status, you'll be reporting everything as capital gains on Schedule D, which aligns perfectly with listing "Investor" as your occupation. Don't overthink it - the IRS has seen plenty of people who left traditional jobs to trade full-time. As long as you're accurately reporting all your gains/losses and paying the right taxes, your occupation designation won't be an issue. I'd stick with "Investor" and move forward with confidence.

I went through this exact same situation two years ago when I transitioned from my corporate job to full-time trading. After consulting with a tax professional and doing extensive research, I can confirm that "Investor" is absolutely the correct occupation to list. The distinction is important: investors buy and sell securities to generate capital gains/losses (which is what you're doing), while traders who qualify for trader tax status are considered to be in the business of trading and report their income differently on Schedule C. Since you mentioned you don't qualify for trader tax status, you'll be reporting your gains and losses on Schedule D and Form 8949 - which is exactly what investors do. Your occupation designation should align with how you're filing your taxes. One additional tip: keep good records of your trading activity and any investment-related expenses. While most investment expenses aren't currently deductible, having organized records shows you're treating this seriously as your occupation, not just as a hobby. Don't worry about audit flags - the IRS sees plenty of people who trade as their primary income source. As long as you're accurately reporting everything and paying the appropriate taxes, listing "Investor" won't raise any red flags.

FYI - TurboTax handles 1099-B and Form 8949 reporting much better than TaxSlayer in my experience. I switched this year after having similar frustrations. They have a direct import feature that works with most brokerages, and they're much clearer about how to handle wash sales and basis reporting. Yes, it costs more, but when you're dealing with investment transactions, the extra guidance is worth it. They also have much better support if you get stuck.

I had the exact same frustration with TaxSlayer and stock reporting last year! One thing that helped me was understanding that you absolutely do NOT need to report every single transaction if your broker already reported the basis to the IRS (which Fidelity usually does for covered securities). Here's what worked for me: Look at your 1099-B and find the summary totals at the bottom of each section (short-term vs long-term). If the "basis reported to IRS" box is checked, you can enter these as summary transactions in TaxSlayer instead of individual trades. For the dates, use "VARIOUS" for acquisition date and 12/31/2023 for sale date when doing summary reporting. This is totally acceptable and saves hours of data entry. For wash sales in TaxSlayer: When you're entering your 1099-B info, there's a section that asks about "adjustments" - that's where the wash sale amounts go. Just enter the total wash sale adjustment from your 1099-B summary (it should be clearly labeled). The key is to match exactly what's on your 1099-B totals - don't overthink it! TaxSlayer will generate Form 8949 automatically based on what you enter.

Has anyone here used TaxAct for partnership returns? Their software is cheaper than the bigger names but I'm not sure if it handles all the schedules properly.

Just wanted to share my experience since I was in a similar situation last year with a small LLC partnership. You're absolutely right that the IRS website can be confusing! The key thing that helped me was realizing that Form 1065 is basically a "package deal" - all those schedules (B-1, B-2, and the K-1s) are considered part of the main return and go to the same address. Think of it like sending a book with multiple chapters rather than separate documents. One tip that saved me stress: if you're getting close to the deadline, definitely consider e-filing instead of mailing. The confirmation is instant, and you don't have to worry about postal delays or whether the IRS actually received your package. Most basic tax software can handle a simple 50/50 partnership return like yours. Also, make sure you keep copies of everything for your records, especially those K-1s since you'll both need them for your personal tax returns. Good luck with the filing!

Has anyone tried just using the IRS "Get Transcript" tool to download the actual 1099Bs? Sometimes the online version shows more details than what they mail you.

One thing that helped me was creating a spreadsheet with all the mystery 1099Bs from my transcript, then systematically going through each investment account statement from the tax year. I included columns for the last 4 digits of the TIN, the dollar amounts, and transaction dates. What I discovered was that some of my "mystery" 1099Bs were actually from dividend reinvestment plans (DRIPs) that I had completely forgotten about. These often get their own separate reporting even when they're associated with stocks you hold in your main brokerage account. Also check if you have any old retirement accounts or 401(k)s from previous employers. Sometimes when you do rollovers or transfers, there can be interim reporting from custodial companies that generates 1099Bs you wouldn't expect. The amounts are usually small but they still need to be accounted for properly. If all else fails, you might want to consider getting a tax professional to help reconcile everything. It's frustrating to pay for something you feel like you should be able to figure out yourself, but the peace of mind is worth it when you're dealing with dozens of forms.