Where did you find receipt books like that? I've looked at office supply stores but only find standard ones without those labels.

I actually got mine custom-printed online. It wasn't very expensive - about $15 for a pack of 5 books. Just search for "custom receipt books" and you'll find several companies that let you design your own layout. I added fields for "Item Condition" and "Serial Number" too since those are important in the computer parts business.

This is terrible advice. The IRS absolutely wants to see receipts for business expenses. A Google Doc you created yourself isn't sufficient proof of purchases during an audit.

Do you need to make quarterly payments for side hustle income? I heard somewhere that you need to if you'll owe more than $1,000 at tax time, but not sure if that's true.

Yes, that $1,000 threshold is correct. If you expect to owe more than $1,000 in taxes when you file your return, you should make quarterly estimated tax payments to avoid an underpayment penalty. For side hustles, a good rule of thumb is to set aside about 30% of your profit for taxes (covers both income tax and self-employment tax for most people). You can use Form 1040-ES to calculate and pay your quarterly taxes. The due dates are April 15, June 15, September 15, and January 15 of the following year. Better to start paying quarterly now than get hit with a big bill plus penalties!

Thanks for the tip about the separate account! That actually makes a lot of sense. Do you have a recommendation for a good expense tracking app that's simple to use? I'm not the most tech-savvy person tbh.

I use QuickBooks Self-Employed and it's pretty straightforward even for non-tech people. It links to your bank accounts and credit cards, then lets you swipe expenses left or right to categorize them as business or personal. The basic version is like $7/month which is totally worth it for the headache it saves. If you want something free, even the basic version of Mint can work if you create tags for your different side hustles. But honestly, whatever you choose, the most important thing is consistency - spend 5 minutes every few days categorizing transactions while they're fresh in your memory!

Yep! I used the Get Transcript tool on irs.gov last month. You need to request the "Tax Return Transcript" option, not the account transcript. It shows the filed 8606 information though sometimes it's just the line entries, not the actual form image. Was enough for me to see where I messed up my basis calculations.

Perfect, thanks! Just tried it and was able to get my transcripts. You're right - it shows the numbers but not the actual form. Still helpful though - I can see I definitely carried forward the wrong basis amount for my backdoor Roth in 2021. Ugh, time to fix it.

Are the Tax Institute guides updated every year? My main concern is spending money on resources that might become outdated with tax law changes.

Yes, they update them annually to reflect the latest tax legislation and rulings. That's actually one of their big selling points - you're getting the most current information, which is crucial in tax accounting where rules change frequently. The recent editions include all the changes from the last federal budget and recent ATO interpretations. Even if you buy last year's edition at a discount, the core concepts remain valid, but for specifics like rates and thresholds, you'd want the current version.

I second this! PwC's summaries are gold. Also check out the free CCH IntelliConnect resources if your uni library subscribes - saved me heaps of $$ on books.

Thanks so much for sharing your experience! Can I ask how you found your EA? Did you just Google or use a specific service? And did they require payment upfront for all the returns?

I found my EA through the National Association of Enrolled Agents website (naea.org) which has a directory you can search by location. I interviewed three before picking one - which I highly recommend doing. Some were much more knowledgeable about unfiled returns than others. My EA required a 50% deposit upfront and the remainder when the returns were completed, before filing. She explained that different EAs have different payment policies, but most will want at least some payment before beginning work. One nice thing was she gave me a clear flat-rate price per return rather than charging by the hour, so there were no surprises.

I tried using TurboTax for multiple unfiled years and it was a nightmare. The software isn't really designed for prior year returns, especially multiple years at once. I ended up making mistakes that triggered notices from the IRS. If you have very simple returns (just W-2 income, standard deduction), it might work, but even then, you have to purchase the previous year's software separately for each year you need to file. It ended up costing almost as much as hiring a professional would have, with none of the expertise.