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Another option nobody mentioned is adjusting your income timing if possible. I run a small consulting business and I deliberately delay some December invoices to January when it makes sense tax-wise. Not saying you should hide income, but legitimate timing of income recognition can help balance your tax liability between years.
Can you really just decide which year to count income in? I thought you had to report income in the year you receive it, not when you decide to invoice for it?
It depends on your accounting method. If you're on a cash basis (which most small businesses and freelancers are), you report income when you receive it, not when you earn it. So if you complete work in December but don't send the invoice until January, you'll receive and report that income in the following tax year. This is totally legitimate as long as you're not artificially manipulating when you actually receive payments. You can't deposit a check and not record it - that would be illegal. But you can time when you bill clients and when you make business purchases within reason.
Has anyone used the annualized income installment method mentioned earlier? I'm a seasonal worker too (landscaping business) and make most of my money April-September. Is it worth the hassle of filling out that extra form?
I've used it for clients with seasonal businesses. It's more paperwork (Form 2210 Schedule AI), but it can be worth it if your income is heavily concentrated in certain periods. Basically, you calculate your required payment for each quarter based on what you actually earned that quarter, not 1/4 of your annual income.
I've done this exact adjustment in ProSeries for clients for years. Go to the Form 8582 worksheet in ProSeries, and look for Line 16 of the actual form (within the software). There should be an override field where you can enter your desired allowed loss amount instead of the calculated amount. Important: Make sure you keep detailed records of your calculations and remaining carryforwards. Create a supporting statement in ProSeries explaining your calculation and why you're choosing to limit the allowed losses. This will help if you ever get questioned about it.
Thanks for the specific guidance on ProSeries! When I create the supporting statement, should I explicitly mention the AMT avoidance strategy, or just document the calculation of limited PAL?
I would recommend documenting both. In your supporting statement, first detail your calculation of the limited PAL amount - showing the total available, the amount you're choosing to use, and the remaining carryforward. Then I would also briefly explain the tax planning strategy - that you're limiting the PAL utilization to minimize Alternative Minimum Tax impact. This shows the IRS there's a legitimate tax planning purpose behind your decision. It's completely legal tax strategy, and being transparent about it actually strengthens your position if there's ever a question.
Has anyone considered the impact this might have on passive activity grouping elections? If you're selectively limiting losses on certain activities, could it affect how the IRS views your grouping?
Good point. If you've made grouping elections for your passive activities, you should be consistent in how you treat the entire group. You can't cherry-pick which specific property's losses to use within a grouped activity. You would need to proportionally limit losses across the grouped activities.
Another option you might consider is having your friend make individual $1,000 payments directly to each person. That way, you avoid having the entire $10k hit your account at once. If each person just gets their $1,000 directly, it's less likely to trigger any reporting requirements since it's under typical thresholds, and you don't have to worry about explaining why you received $10k that mostly wasn't yours. Just a thought to potentially simplify the whole situation!
But don't some payment apps have daily or weekly transfer limits? My PayPal only lets me send like $2-3k per week without upgrading or something. Might be annoying for the friend to space it out over time.
You're right about the limits on some platforms. Venmo's standard limit is $4,999.99 per week for person-to-person payments, so the friend would need at least 3 weeks to pay everyone individually if using Venmo. PayPal has similar restrictions as you mentioned. Banks typically have higher limits for Zelle transfers, often $2,000-$5,000 daily depending on the bank. Your friend could potentially use multiple payment methods or speak with their bank about temporarily increasing limits if they wanted to make all payments quickly.
Has anyone mentioned gift tax implications? If someone gives you more than $17,000 in a year (2023 annual exclusion amount), they're supposed to file a gift tax return. I know this isn't technically a gift since it's repayment, but could the IRS see it that way if they just notice a large transfer?
This is a good question, but no, the gift tax wouldn't apply here. The IRS defines gifts as transfers made without receiving full consideration (value) in return. In this case, the $10k is repayment of money previously provided - it's settling a debt, not a gift. Even if the IRS initially questioned it, you would explain that this was repayment of a loan. That's why documentation of the original arrangement is important. Text messages, emails, or even witnesses who can confirm the nature of the original transaction can help establish this wasn't a gift.
From my experience as someone who made this switch at around $65k, here are some practical costs you should budget for: 1. Initial LLC formation: $200-300 depending on state 2. S-Corp election: Free (just file Form 2553) 3. Annual LLC fees: Varies by state ($150 in my state) 4. Payroll service: I use Gusto which costs about $45/month ($540/year) 5. Accountant: My tax preparation went from $350 to $1,200 annually 6. Bookkeeping software: $25/month for QuickBooks ($300/year) So my additional annual costs are around $2,190. But I'm saving about $3,800 in SE taxes by having a $48k salary with the rest as distributions. So net benefit around $1,600 per year. The time commitment is also significant - about 2-3 hours per month dealing with payroll, bookkeeping, etc. that I didn't have before.
Did you have to get a separate business bank account and strictly separate personal vs business expenses? That part seems complicated.
Yes, keeping separate accounts is absolutely essential. I have a dedicated business checking account, savings account, and credit card that I ONLY use for business expenses. This creates what accountants call a "clean separation" between personal and business finances. This separation is critically important when you have an S-Corp to avoid having your corporate veil pierced in case of legal issues. It also makes bookkeeping much easier and helps prove to the IRS that you're operating a legitimate business. Mixing personal and business expenses is a huge red flag that can trigger audits.
Has anyone used a PEO (Professional Employer Organization) instead of regular payroll for their S-Corp? I'm hearing they can be cheaper than traditional payroll services and they handle all the compliance stuff.
I use Justworks for my S-Corp and it's been amazing. They handle all payroll taxes, compliance filings, and even offer health insurance options that are better than what I could get as a tiny business. It costs a bit more than basic payroll ($49/month per employee) but the time savings and reduced stress are worth it.
Layla Mendes
Direct File is still in its pilot phase for 2025 filings. The IRS is planning to expand it to include state returns in future years, but they started with just federal to work out the kinks. This is actually pretty clearly stated during the signup process, but a lot of people miss it. You're definitely not alone in being confused! Several of my friends had the same issue. For what it's worth, I think the IRS should make this limitation MUCH more obvious during the filing process.
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Lucas Notre-Dame
ā¢Do we know which states will be included when they eventually expand? I'm in Texas so we don't have state income tax anyway, but curious about the rollout plans.
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Layla Mendes
ā¢The IRS hasn't announced specific states that will be included in future Direct File expansions. The rollout will likely depend on which states are willing to partner with the federal system, so it will vary. For Texas residents like yourself, you're actually in a good position since you don't have state income tax to worry about. Direct File is already a complete solution for you. The taxpayers who have to deal with this two-step process are those in the 41 states plus DC that have income tax filing requirements.
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Aria Park
Check your state's tax website! Most states (like 22 of them I think) have their own free filing portal separate from the IRS. I used Direct File for federal and then my state's portal for state taxes and paid $0 total. Took a little longer having to enter info twice but saved me like $50 compared to TurboTax.
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Sophia Nguyen
ā¢Thanks for the tip! I wish I'd known this before paying for TurboTax. Will definitely check Colorado's website for next year. Did you have to re-enter all your information or was there a way to import data from your federal return?
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