Is there a difference between a regular CPA and an "Enrolled Agent"? How do you find someone who specializes in tax resolution specifically?

An Enrolled Agent (EA) is a tax professional who's been licensed by the IRS specifically to represent taxpayers. They've passed comprehensive exams on tax matters and often specialize in tax resolution. While many CPAs are excellent with taxes, EAs focus exclusively on tax issues and representation before the IRS. To find someone specializing in tax resolution, search for "Enrolled Agent tax resolution" in your area, or check the National Association of Enrolled Agents website. You can also search for CPAs who specifically mention tax resolution services. Always check reviews and ask about their experience with cases similar to yours. A good tax resolution specialist should offer a free initial consultation to discuss your situation before charging fees.

This is so true! I had a similar situation where I was trying to set up a payment plan for about $30k in back taxes but kept getting rejected because I had a missing return from 3 years prior. Once I filed that last return, everything went much smoother.

9 Did your wife have to register her business officially before claiming those deductions? I'm wondering if my husband needs a business license or official DBA name before we can start claiming his equipment purchases.

22 No formal business registration was required for tax purposes, though she did get a business license because our city requires one. For the IRS, you don't necessarily need a formal business entity to be considered "in business" and claim deductions on Schedule C. What mattered more was showing evidence of actually being in business - having clients, advertising services, maintaining business records, etc. The IRS looks for a profit motive and genuine business activity. Your husband should document when he transitions from just learning to actually seeking clients, even if it's just a few at first while still apprenticing.

19 I'm not the OP but I've been wondering about this too. Does forming an LLC actually help with tax deductions or is it mainly for liability protection? Is it worth the filing fees if you're just starting out?

Thanks for sharing your experience! Did filing the 4810 form trigger any kind of review or did they just accept it and that was that? Also, did you have to wait the full 18 months before considering everything officially "closed" with the IRS?

In our case, they simply accepted the form and we never heard anything from them afterward. There was no additional review triggered by filing Form 4810. We didn't have to wait the full 18 months to distribute assets or anything like that. The form just means they have 18 months to audit if they want to, but it doesn't prevent you from closing the estate otherwise. Our lawyer advised us that after about 6 months with no contact from the IRS, the chances of them looking at anything were extremely low. We considered everything effectively closed at that point, though technically the 18-month window was still open.

When we filed Form 4810 for my grandfather's estate, we sent it certified mail with return receipt so we'd have proof of when the IRS received it. The IRS doesn't typically send any confirmation that they've processed the form or approved your request. The 18-month period starts from when they receive a properly completed form.

Thanks, that's really helpful to know! I'll definitely send it certified mail then. One more thing - did your attorney recommend filing this right after submitting the estate's final tax return, or is there a specific waiting period?

So would selling stocks or crypto with capital gains trigger this? I did make about $3k in stock gains last year that I paid taxes on when I filed, but I didn't think that would trigger getting a 1040-ES for the next year.

Yes, capital gains from stocks or crypto could definitely trigger this if you ended up owing taxes when you filed. The $3k in stock gains without tax withholding would create a tax liability, and if your total tax due when filing was over $1,000, that would typically trigger the 1040-ES forms for the following year. The IRS essentially is saying "we noticed you had income without withholding last year, so we expect you might have similar income this year - please make estimated payments quarterly instead of waiting until tax time." It's their way of making sure you're paying taxes throughout the year on income that doesn't have automatic withholding like a W-2 job would.

If your tax situation is going to be significantly different this year (like you won't have the extra income that triggered it), you can technically ignore them. BUT - if you end up owing more than $1,000 when you file next year, you could face underpayment penalties. The safe approach is to either make the quarterly payments OR increase your withholding at your regular job to cover any expected tax. The IRS doesn't care how you pay throughout the year, just that you do.

Wouldn't quarterly payments be a hassle to calculate though? How do you figure out exactly how much to pay each quarter?

It's actually much easier than it sounds. I just take what I earned from my side job each quarter, multiply by about 25% to be safe, and pay that amount. You can use Form 1040-ES which has a worksheet to calculate it precisely. For me it's less hassle than adjusting my W-4 constantly, especially since my side income varies quite a bit from month to month. Plus you don't have to worry about over-withholding and waiting for a refund - you just pay what you actually owe.

But doesn't checking the multiple jobs box on both W-4s cause over-withholding? That's what my accountant told me.