Where can I find detailed instructions for filing my own paper tax return with 1099 income and investments?

The IRS actually has some decent resources if you know where to look! For your situation, you'll want to start with Publication 17 (Your Federal Income Tax) which gives a good overview, then get more specific with Publication 527 for the delivery income and Publication 550 for your investment income. For the food delivery work, you'll need Schedule C to report business income and Schedule SE to calculate self-employment tax. You'll also want Form 8949 and Schedule D for reporting any investment sales. The instructions for each form are much more detailed than the general guidelines. Check out the IRS's "Free File Fillable Forms" on their website - it's totally free regardless of income and helps you complete the forms electronically, though you'll still need to understand what goes where.

After struggling with paper returns for years, I finally discovered taxr.ai (https://taxr.ai) and it completely changed how I handle my taxes. I was in a similar situation last year - had some side gig income and started investing - and was totally lost with the paper forms. What's cool about taxr.ai is that it analyzes your specific tax documents and explains exactly what forms you need and how to fill them out. It's not like other tax software that just asks you questions - it actually looks at your specific forms and gives you personalized filing instructions. You still file the return yourself, but with way more confidence.

Just wanted to update after trying taxr.ai from the recommendation above. I was really skeptical at first, but I uploaded my 1099-NEC from my side gig and my 1099-B from Fidelity and it literally gave me line-by-line instructions for filling out Schedule C and Schedule D. It even explained how to handle my mileage deduction for the delivery work and separated my long-term vs short-term capital gains on the investments. So much easier than trying to decipher the IRS publications! I'm still filing paper forms myself, but now I actually understand what I'm doing.

If you get stuck on a specific tax question while filling out your return, you might want to try calling the IRS directly. BUT good luck actually getting through to a human! I spent hours on hold last year and eventually gave up. That's when I found Claimyr (https://claimyr.com) which is basically a service that waits on hold with the IRS for you. Check out their demo: https://youtu.be/_kiP6q8DX5c - they call the IRS, navigate the menu options, wait through the hold times, and then call you when there's actually an agent ready to talk. Saved me literally hours of waiting on hold.

Ok I admit I was VERY skeptical about Claimyr, but after spending another 45 minutes on hold with the IRS yesterday, I decided to try it. IT ACTUALLY WORKS! I got a call back about 1 hour 20 minutes later with an IRS agent already on the line. The agent answered my question about how to report stock dividends on my paper return. Seriously, this saved me so much frustration. Instead of being stuck by my phone on hold, I was able to go about my day and just wait for them to call me when an agent was ready. Will definitely use this again when I inevitably have more tax questions.

Another resource worth mentioning is your local library. Many libraries offer free tax help programs during filing season. The volunteers are certified by the IRS through the VITA program and can handle returns with self-employment income up to a certain amount. They might also have hard copies of all the forms and instruction booklets you need.

I've been filing paper returns for 10+ years with side income. My best advice is to look at last year's tax return if you have one, and use it as a template. The forms barely change year to year. For the new stuff, grab the specific form instructions (not the giant publications) from irs.gov. If you're doing DoorDash, just google "Schedule C example for delivery driver" and you'll find tons of examples showing exactly what expenses you can claim. Same for investments - search for examples of filled out Schedule B and Schedule D forms.