How exactly do I calculate the right amount of extra withholding to put on my W-4? Is there a formula or calculator you'd recommend?

A simple approach is to take your expected freelance income for the year and multiply it by 30% (which covers both income tax and self-employment tax for most people). Then divide that amount by the number of pay periods you have at your regular job. For example, if you expect to make $5,000 in freelance income and get paid bi-weekly (26 pay periods), you would calculate: $5,000 × 0.30 = $1,500 in estimated taxes ÷ 26 pay periods = about $58 extra withholding per paycheck. You'd put that amount on line 4(c) of your W-4 form. The IRS also has a tax withholding estimator on their website that's more precise if you want to get it exactly right.

I've been doing freelance work for years and never made quarterly payments (don't tell the IRS lol). Never had any penalties. Is it really that important?

Is there a deadline for the IRS to process prior year returns and issue refunds? I filed my 2021 return about 2 months ago and haven't heard anything.

The IRS doesn't have a specific deadline for processing prior year returns, but they typically take longer than current year returns. Prior year returns are usually processed manually rather than through their automated systems, which adds to the processing time. Generally, you can expect a processing time of 6-12 weeks for paper returns, but for prior year returns, it can sometimes take 16 weeks or more. If it's been more than 16 weeks since you submitted your return, you can call the IRS or use their "Where's My Refund" tool, though that tool sometimes doesn't work well for prior year returns.

Actually I think there was a separate phaseout for the additional amount over $2,000. The original $2,000 CTC didn't start phasing out until $200k single/$400k married.

You're absolutely right, thanks for that correction! The 2021 Child Tax Credit had two different phase-out thresholds: The enhanced portion (the extra $1,600 for kids under 6 or $1,000 for kids 6-17) started phasing out at $75,000 for single filers and $150,000 for married filing jointly. The base $2,000 credit didn't start phasing out until $200,000 for single filers and $400,000 for married filing jointly. This was one of the more confusing aspects of the 2021 tax changes. Thanks for pointing that out!

I've heard about CNC status but wasn't sure if it would apply in this case. Would the IRS consider CNC even if my client has consistent income? Their issue is more that the total amount is overwhelming rather than having no income at all.

CNC status is based on ability to pay after necessary living expenses, not just on having income. If your client's income is being consumed by reasonable living expenses with nothing left over, they could still qualify. The IRS uses their Collection Financial Standards to determine what counts as necessary expenses. Have your client document all their actual expenses - housing, utilities, food, healthcare, transportation, etc. If these legitimate expenses leave little to nothing for tax payments, they have a case for CNC status even with steady income. The IRS would rather put someone in CNC temporarily than force them into a payment plan they can't maintain.

Be careful with this advice! The 10-year clock doesn't start until the tax is assessed, which can't happen until the return is filed. For unfiled returns, the clock hasn't even started ticking yet. Plus, certain actions can extend that 10-year period, like requesting an installment agreement or filing bankruptcy.

The charitable remainder trust is interesting but wouldn't work in my case since I don't own the asset - it's just a profit share agreement that pays out when the company sells. Could opportunity zone investments still work after I receive the payout? How quickly would I need to invest in one after getting the profit share payment?

You're right about the CRT - it only works for assets you currently own, not future payments you'll receive. Sorry I missed that detail. For opportunity zone investments, you generally have 180 days from realizing the capital gain to reinvest into a qualified opportunity fund. So you could potentially use this strategy after receiving your profit share payout. The deferral benefits aren't as strong as they were initially, but you can still defer the tax until 2026 and potentially reduce your taxable gain by 10% if you hold the investment long enough.

Installment sales are complicated though right? I tried to do one last year and my tax software couldn't handle it - ended up needing to pay an accountant extra to file correctly.

Thanks for sharing your experience! So with your holding LLC structure, do you just file one partnership return for the holding LLC, or do you still need to file for each property LLC as well? I'm trying to understand the administrative burden.

With my structure, I only file one partnership return (Form 1065) for the holding LLC. The individual property LLCs are treated as "disregarded entities" for federal tax purposes since they're single-member LLCs owned by the holding LLC. This significantly reduces tax preparation costs and paperwork. You'll still need to maintain separate books for each property for good management practices, but the tax filing burden is much lighter. Note that state requirements vary - some states may require separate filings or have annual fees for each LLC regardless of tax status. In my case, the administrative simplification at the federal level has been a big advantage.

That's a really important consideration. For real estate investors, the QBI deduction can offer up to a 20% deduction on qualified business income. With pass-through entities (LLCs taxed as partnerships, S Corps, or disregarded entities), you generally preserve your ability to claim this deduction. C Corps aren't eligible for the QBI deduction, which is another reason they're often not ideal for real estate holdings. Also, if your income is above certain thresholds, having your properties in the right structure becomes even more important to maximize QBI benefits.