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Unpopular opinion maybe but I think the whole estimated tax system is outdated and ridiculous. W2 employees get taxes automatically withheld but self-employed people have to calculate all this complicated quarterly stuff or face penalties? The tax code shouldn't punish entrepreneurs and freelancers with extra complexity and gotcha penalties.
THANK YOU! That's exactly how I feel. It's like they're deliberately making it hard for self-employed people. I'm trying to run a business and now I have to be an amateur tax accountant too?
Pro tip: One way to avoid these penalties entirely is to increase your withholding from a W2 job if you have one alongside your self-employment income. The IRS treats withholding as if it happened evenly throughout the year, even if it's all withheld in December! So if you're behind on estimated payments but have a W2 job, you can adjust your W4 to withhold more from your remaining paychecks for the year. This can eliminate or reduce penalties even if the actual payment happens late in the year.
This is genius! I have a part-time W2 job along with my consulting business. So I could potentially just have them withhold extra from my W2 in Q4 and it would count as if I'd been paying it evenly all year? Would save me so much headache with quarterly calculations.
Exactly! The IRS treats withholding from paychecks as if it occurred evenly throughout the year, even if you adjust your W4 in December to withhold a larger amount from your final paychecks. This is a completely legal strategy that many tax professionals recommend. Just be careful not to withhold so much that you create financial hardship for yourself. You'll want to calculate approximately how much you'll owe for the year, subtract what you've already paid through estimated payments, and then divide the remainder by your remaining paychecks to determine how much extra to withhold per paycheck.
Everyone's talking about penalties, but don't forget state requirements too! Depending on your state, you may have separate W-2 filing requirements with different deadlines and penalties. I learned this the hard way when I got hit with state penalties even after resolving my federal issue.
Which state are you in? I'm in California and haven't even looked into the state requirements yet. Do you file W2s with the state tax agency separately?
I'm in New York, but most states have their own requirements. In California, you'd need to submit your W-2s to the Employment Development Department (EDD), not just the federal SSA. California actually has some of the stricter penalties for late filing - they can charge $50 per W-2 plus potentially 10% of the tax that was withheld if you're very late. Their deadline is the same as the federal one (January 31st), but the submission process is completely separate. Check the California EDD website for their specific filing instructions.
This probably doesn't help you now, but for next year look into small business payroll services like Gusto or QuickBooks Payroll. I was in the exact same position as you last year - health issues, late filing, panicking about penalties.
Are those services expensive? I only have 2 part-time employees and do everything manually because I thought payroll services were overkill.
One thing nobody's mentioned - make sure you're using the right tax years' forms when amending! The Schedule C from 2023 is different than the one from 2014. You need to use the original year's forms for each amendment. You can find old tax forms on the IRS website in their "Prior Year" section.
Thanks for mentioning this! I would have totally messed that up. Do you know if I need to include all the original attachments again or just the ones I'm changing?
You only need to include the forms and schedules that you're changing with your Form 1040X. So definitely the Schedule C for your business expenses, but if you're not changing other aspects of your return, you don't need to include those other forms again. Also, you'll need to file a separate 1040X for each tax year you're amending. Don't try to combine multiple years on one form - the IRS will reject it.
Don't forget to include a detailed letter explaining exactly why you're amending! I amended taxes from 8 years ago and they initially rejected it until I sent a very specific explanation letter with my documentation. Be super clear about the tax resolution company's error and why you're just now fixing it.
Good advice. Also worth noting that the IRS generally has 10 years from the date of assessment to collect taxes owed. So depending on exactly when these returns were filed/assessed, the collection statute of limitations might be approaching.
One thing nobody has mentioned yet - have you considered forming an LLC to hold the property? My partner and I did this when we bought our home together. The LLC holds the title, we each own 50% of the LLC, and we have an operating agreement that specifies all the details about payments, what happens if we break up, etc. This approach has some advantages with liability protection and makes the tax situation cleaner in some ways. But there are setup costs and annual fees to maintain the LLC, so it might not be worth it depending on your situation.
Wouldn't using an LLC mean losing the mortgage interest deduction? I thought you could only deduct mortgage interest on your primary residence if you personally own it, not if it's owned by an LLC?
You're right to question this - an LLC typically would cause you to lose the mortgage interest deduction for a personal residence. What we actually did was create a partnership agreement rather than a full LLC (I simplified in my original comment). The partnership agreement gives us similar protections in terms of clearly defining ownership and responsibilities, but allows the property to remain in our personal names for tax purposes. This way we each get to deduct our portion of the mortgage interest while having clear documentation of our arrangement. Tax rules around entity structures can get complicated, so definitely consult with a tax professional before going this route.
Has anyone mentioned gift tax issues yet? My partner and I ran into this when we bought together. If one person is making substantially larger payments toward the mortgage than their ownership percentage, the IRS might consider the excess amount a gift, which could have gift tax implications.
I don't think that's correct. The annual gift tax exclusion is $17,000 per person for 2023 (probably higher for 2025), and it's only an issue if you exceed that amount. Plus, you'd have to file a gift tax return but probably wouldn't owe any actual tax unless you've used up your lifetime exemption, which is over $12 million.
Millie Long
An important thing to watch out for with rental property K-1s is the passive activity loss limitations. Since you mentioned you do "absolutely nothing" to manage the property, your loss is definitely passive and may be limited. If your modified adjusted gross income is under $100,000, you might be able to deduct up to $25,000 of rental losses under the active participation exception. But that phases out completely when your MAGI hits $150,000. If you're above that threshold, those losses get suspended until you either have passive income or dispose of your interest in the partnership.
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KaiEsmeralda
ā¢Does receiving the K-1 automatically make you a "material participant" in the business? I'm in a similar situation with a family business and don't know if I can claim the losses.
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Millie Long
ā¢No, receiving a K-1 does not automatically make you a material participant. Material participation is determined by how much time and effort you put into the activity. There are seven tests for material participation in IRS Publication 925, but generally you need to work 500+ hours in the activity during the year to be considered a material participant. For rental activities specifically, they're automatically considered passive regardless of your participation hours, unless you qualify as a real estate professional (which requires 750+ hours in real estate activities and more time in real estate than any other occupation).
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Debra Bai
Does anyone know if these K-1 losses affect the QBI deduction? I have a similar rental partnership and heard something about QBI being reduced by losses.
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Cassandra Moon
ā¢Yes, rental losses can affect your QBI (Qualified Business Income) deduction. Under Section 199A, QBI is calculated for each business activity and can be reduced by losses. If your rental activity is considered a qualified trade or business (which depends on several factors), the net loss would result in no QBI deduction for that activity. Additionally, net losses from qualified businesses can offset QBI from other profitable qualified businesses, potentially reducing your overall QBI deduction. It gets complicated quickly, which is why tracking these losses properly is so important.
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