Do you need to make estimated tax payments if you have a decent amount withheld from your W-2 salary? Like could I just increase my W-2 withholding and skip the quarterlies?

Yes, you absolutely can increase your W-2 withholding instead of making separate quarterly payments! This is actually a great strategy many S-corp owners use. You can use the higher withholding from your S-corp salary to cover your tax liability on both your salary AND distributions. Just complete a new W-4 form requesting additional withholding to cover the tax on your distributions. The IRS doesn't care whether the tax comes through withholding or estimated payments, as long as you're paying enough throughout the year to avoid underpayment penalties.

I've been using QuickBooks Online for my S-corp for 3 years now. It's not perfect but it lets you categorize distributions vs owner draws properly and generates decent reports for tax time. Just make sure you set it up correctly from the beginning!

Thanks for sharing your experience! Could you clarify which specific tax form or schedule you used to list these expenses? And did you have to itemize deductions or was this handled differently?

I used Form 8863 (Education Credits) and claimed the expenses as part of my qualified education expenses for the American Opportunity Credit. The great thing is you don't need to itemize deductions to claim education credits - they're available even if you take the standard deduction. The form has a line specifically for required course materials, which is where these project expenses can fit. Just make sure you have documentation that clearly shows the project was required for your degree program!

This is critical advice! I got audited because I used outdated tax advice from a blog post. Always check that you're looking at the most current IRS publications. For education expenses, Publication 970 is the bible - they update it every year.

Wouldn't this definitely cause problems with OP staying in the industry though? The DOL investigation would name them specifically right? Unlike the IRS where there's at least some level of confidentiality?

You're right that there's less anonymity with a state labor board complaint. They typically inform the employer who filed the complaint during the investigation process. That said, there are strong anti-retaliation laws that make it illegal for your former employer to badmouth you in the industry or interfere with future employment. Whether this causes industry problems really depends on your specific situation - how vindictive your former employer might be, how large the industry is in your area, and how much power they have within it. It's definitely something to weigh carefully based on your individual circumstances and tolerance for potential conflict.

I did try talking to her about it while I was still working there. She blamed her accountant for all the mistakes but never actually fixed anything. When I brought it up again after getting my W2 and seeing all the problems, she got defensive and basically said her books were correct and I must be mistaken. That's when she cut my pay citing "tax errors" that needed to be "corrected" going forward. I've been hesitant to reach out again since quitting because our last conversations were pretty tense. But maybe a formal letter outlining the issues with copies of the checks would be worth trying before filing anything official?

A formal letter is definitely worth trying. Make it professional, not accusatory, and focus on the factual discrepancies with your documentation attached. Suggest that you're hoping to resolve this directly before having to involve tax authorities. Send it certified mail so you have proof she received it. Give a reasonable timeframe for response (like 14 days). This approach gives her one last chance to correct things, and if she doesn't respond, you've created additional documentation of your good-faith efforts to resolve the situation before filing official complaints. That paper trail of attempting resolution can be beneficial if you do need to escalate things.

Have you ever had to provide these digital records to the IRS? I'm worried they might not accept them during an actual audit. Also, what software do you use for the scanning and organization?

I had a correspondence audit two years ago, and they fully accepted my digital documentation without issue. I submitted everything electronically through their portal and it went smoothly. I use a combination of a decent scanner app on my phone for receipts on the go, and a document scanner with automatic feed for batch scanning larger documents. For organization, I create yearly folders with subfolders for income, expenses, deductions, etc. I'm careful to make sure everything is clearly labeled and searchable. Most important is having a solid backup system - I use both cloud storage and local backups.

What's the deal with property records? I bought a house in 2019 and have all those closing documents taking up space. Can I scan and shred those too?

Property records are definitely in the "keep until you sell the property plus 3 years" category. This includes all your closing documents, records of improvements, and anything that affects your basis in the home. For your 2019 home purchase, these documents are absolutely critical to keep. If you eventually sell the home, you'll need to prove your basis (purchase price plus improvements) to calculate any potential capital gains. While you can certainly scan these for convenience and backup, I'd actually recommend keeping the physical originals of major property documents in a fireproof safe. These are the few documents where having the originals can really matter, especially for title-related paperwork.

That's a really good point about the gift tax exclusion - I hadn't even thought about that angle. My uncle definitely hasn't given me anywhere near the $18,000 limit, so we should be fine there. And yes, you're absolutely right about the management company. Looking closer at my statements, they've already deducted their management fee, cleaning costs, and a couple minor repairs from the rental income reported on the 1099. The expenses my uncle covered were mainly the property taxes, insurance premium, and a major plumbing repair that happened outside the management company's scope. Thanks for pointing this out!

I tried doing this in H&R Block software last year and it was super confusing. It kept asking who paid what and I couldn't figure out where to note that my dad had paid some expenses as gifts. Did TurboTax have a specific field for this?