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Don't overlook enrolled agents (EAs)! They're specifically licensed by the IRS to handle taxes and can represent you in audits, just like CPAs. Often cheaper too. I switched from a CPA to an EA last year (paid $375 instead of $900) and got the same quality service for my freelance business. Whatever you do, don't just use a regular bookkeeper for tax filing. Learned that lesson the hard way and ended up with a $2,100 penalty for incorrect filing. Bookkeepers are great for day-to-day tracking but not always tax experts.
Can EAs help with business structure advice too? Like if I'm trying to decide between LLC vs S-Corp? My main concern is reducing self-employment tax.
Yes, most EAs can definitely help with business structure questions like LLC vs S-Corp decisions. Many specialize in small business taxation and self-employment tax strategies. My EA was incredibly helpful in analyzing when an S-Corp election would make sense for me (generally when netting over $40K in profit). Just make sure you ask them specifically about their experience with business structures and self-employment tax strategies during your initial consultation. Not all EAs focus on business clients - some specialize in other areas like individual taxation or representation during audits.
Something nobody's mentioned yet - ask about their tech setup! My first bookkeeper used actual paper ledgers (in 2025!!) and it was a nightmare. My current CPA has a client portal where I can upload docs anytime and accounting software that syncs with my bank. Sooooo much easier. Also dont forget to ask if they do state taxes too, not just federal. I got burned on that before š©
This is such a good point! I had a CPA who was impossible to reach by email and wanted everything printed. My new tax person uses a secure portal and it saves so much time.
100% agree! The client portal has been life-changing for me. I can just take photos of receipts with my phone and upload them immediately rather than having a dreaded "tax receipt box" that I'd have to sort through later. My current CPA also uses software that automatically categorizes most of my transactions, which means I'm spending about 1 hour a month on bookkeeping instead of 5+ hours. Definitely worth asking about their tech setup during the interview process!
Don't forget about the Taxpayer Advocate Service! They helped me when I was in a similar situation with both back taxes and defaulted student loans. They're an independent organization within the IRS that helps taxpayers resolve problems. Their services are free, and they can sometimes cut through red tape faster than you can on your own. For the student loans, check if you qualify for income-driven repayment plans. Even with older defaulted loans, you may be able to rehabilitate them and then get on an affordable payment plan based on your income.
How do you contact the Taxpayer Advocate Service? I've been dealing with the IRS for months on a similar issue with no progress.
You can reach the Taxpayer Advocate Service by calling 877-777-4778. They also have local offices in every state that you can find on the IRS website. When you contact them, explain that you're experiencing financial hardship due to the situation and that your attempts to resolve it through normal IRS channels haven't been successful. Be prepared to provide documentation of your financial situation and all your attempts to resolve the issue with the IRS directly. They tend to prioritize cases where there's a demonstrable financial hardship or where the standard IRS procedures have failed multiple times.
Something important to consider - if your student loans are federal, definitely look into the IDR account adjustment that's happening right now. If your loans are as old as you say, you might actually qualify for complete forgiveness under the new rules, especially if they've been in repayment/default for 20+ years.
This is great advice - I just got $32k in loans forgiven through this exact program. The key is to consolidate first if you haven't already, then apply for an income-driven repayment plan and request the account adjustment.
This is actually a really common problem with smaller accounting firms that don't specialize in trust taxation. I'm not excusing their mistake, but many accountants rely heavily on tax software that doesn't automatically flag US Obligations adjustments for state returns. As for how they should make it right - at minimum, they should amend the last 3 years at no charge to you. For the years beyond the statute of limitations, I think it's reasonable to ask for a partial refund of what you paid them, or at least a significant discount on future services. One thing to consider - have they made other mistakes you haven't caught yet? This might be a good time to have another firm review some of your past returns. Trust taxation has a lot of nuances that generalist accountants often miss.
That's exactly what worries me - what else are they missing? The firm has been around for decades and has a good reputation locally, but they might not have enough trust experience. Do you think it's worth having someone do a comprehensive review of all the past returns, or would that cost more than it's worth given the dollars involved?
A comprehensive review could be expensive, potentially costing more than you'd recover. A practical approach might be to have another firm do a focused review looking only at common trust tax issues like the US Obligations, proper allocation of deductions, and correct classification of distributions. Explain the situation and ask for a limited review rather than a full audit of past returns. Focus on the last 3-4 years since those are still amendable. The review might cost $500-800, but if they find additional errors, it could pay for itself. Plus, it gives you peace of mind about other potential issues. Either way, I'd seriously consider finding a new accountant with more trust experience for future returns.
The accounting firm is definitely dropping the ball here. I've been a trustee for several family trusts, and US Obligations adjustments are basic stuff. Have you looked into whether they're properly handling other trust-specific items? Things like: - Proper allocation of expenses between income and principal - Correctly applying the 65-day rule for distributions - Properly documenting charitable deductions - Handling any foreign investments correctly If they missed something this fundamental, I'd be concerned about their overall competence with trust taxation.
One thing nobody's mentioned - your roommate should check if her employer made an error or if she filled out her W-4 incorrectly. The W-4 is the form that tells employers how much to withhold, and if she claimed "exempt" or put too many allowances, that could explain why nothing was withheld. She should update her W-4 ASAP so this doesn't happen again next year! Even if she gets a refund this time because of credits, she might not be so lucky in the future.
Good point! I'll ask her to look at her W-4. She started this job last January and I'm wondering if she just filled something out wrong when she started. Is there an easy way for her to check what she put on the form?
She can ask her HR department or payroll provider for a copy of her current W-4 on file. Most employers will readily provide this. She can also just look at her pay stub - it usually shows the withholding status or at least the amount being withheld (which in her case would be $0). While she's at it, she should file a new W-4 right away. The form was completely redesigned a few years ago and no longer uses allowances. Instead, it has a more straightforward worksheet approach. The IRS also has a Tax Withholding Estimator tool on their website that can help her figure out exactly what to put on the new form.
Has she been filing as Head of Household? With a kid and making under $50k, she'll probably qualify and that gives a bigger standard deduction than filing as single. Could make a big difference in what she owes.
Ryan Kim
Just want to add that you should make at least a partial payment ASAP even if your full payment plan isn't set up yet. I learned this the hard way last year. The penalties and interest start accruing from the original due date regardless of extensions. You can make a payment directly on the IRS website under "Direct Pay" - just choose "extension" or "installment agreement" as the reason. You don't need to wait for a bill or for your online account to show a balance. The IRS will apply any payment to your account once everything processes.
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Aria Washington
ā¢So I can just go to the IRS website and make a payment even though my account doesn't show any balance due yet? Will they know what to do with my money if I don't have any payment plan details or account numbers?
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Ryan Kim
ā¢Yes, you can absolutely make a payment even if your balance isn't showing yet. The IRS can match payments to your tax account using your Social Security Number, tax year, and payment type. When you go to the IRS Direct Pay website, you'll select the tax year, the reason for payment (select "extension" or "balance due"), and enter your identifying information. The system will know what to do with your payment even without specific payment plan details. The most important thing is to get some payment in before the deadline to reduce the penalties and interest that are starting to accrue.
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Zoe Walker
One thing no one mentioned - be sure to check if your state tax deadline works the same way! I filed a federal extension last year and assumed it automatically extended my state deadline too. It didn't, and I got hit with state penalties.
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Elijah Brown
ā¢This is such an important point! Different states have different rules about extensions. Some automatically grant a state extension if you get a federal one, some require a separate state extension form, and the deadlines can vary too.
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