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Don't sleep on OLT.com (OnLine Taxes). It's under $50 for federal + state, and handles investment sales, 1099s, etc. Interface isn't fancy but gets the job done. Been using it for 5 years with similar tax situation to yours.
Have you used it for reporting inherited stocks? That's the part that's tripping me up with my grandma's investments. Need to make sure I get the cost basis right.
Yes, I've used it for inherited stocks. It handles the stepped-up basis correctly - there's a specific section where you can indicate the shares were inherited and enter the fair market value on the date of death as your basis. It also has a surprisingly helpful help section that explains the inheritance rules clearly. Way better than some of the more expensive options I tried previously that made this unnecessarily complicated.
anybody have thoughts on TaxHawk? its basically freetaxusa with a different name... might work for you if youre having specific issues with the freetaxusa interface but still want the same basic system?
Something to be aware of: if the financial institution already reported the transaction to the IRS as a taxable event using a 1099-R, they are required to issue a corrected 1099-R (often called a 1099-R with the "CORRECTED" box checked). Simply changing their internal paperwork doesn't fix the issue with the IRS. Also, for future reference for anyone inheriting annuities: always be extremely clear about requesting a "direct trustee-to-trustee transfer" not a "rollover" when moving inherited annuity funds. Get confirmation in writing before the transaction processes, and if possible, have the receiving institution initiate the transfer rather than the sending institution.
Is there a time limit on when a financial institution can issue a corrected 1099-R? My mom's situation happened almost 2 years ago and we're just now discovering the mistake.
There's technically no specific time limit for a financial institution to issue a corrected 1099-R. They can (and should) correct erroneous information even years later. For your situation with your mom, you generally have 3 years from the original filing deadline to file an amended return to correct mistakes. So even at 2 years out, you still have time to get this fixed. The financial institution may be resistant since it creates extra work for them, but they are obligated to provide accurate tax reporting. Be persistent and escalate to management if needed.
Has anyone successfully had the IRS waive penalties and interest in a situation like this? I got the financial institution to admit their error, but the IRS is still charging me penalties and interest on the "deficiency" even though they agree I don't owe the base tax anymore.
Yes, I had success getting penalties (but not all interest) waived by requesting penalty abatement due to reasonable cause. I explained that the error was made by the financial institution, not me, and provided their admission letter. The IRS has discretion here and often waives penalties when you can prove the error wasn't your fault.
One thing nobody's mentioned yet - check if your audit is actually being conducted by the IRS or if it's been outsourced to a private collection agency. The IRS has been contracting with private firms for some types of enforcement, and they have different contact procedures. Look carefully at the letterhead and contact info on your audit notice. If it mentions Performant, CBE Group, ConServe, or Pioneer, those are private collection agencies working on behalf of the IRS. In that case, the standard IRS protocols might not apply.
That's interesting - I just double-checked and my notice is definitely from the IRS directly. It has the official Department of Treasury/IRS letterhead and mentions the specific IRS tax examination department. But this is good info for others who might be in a similar situation!
Anyone else notice that the IRS seems to be auditing way more returns lately? I've had more clients get audit notices in the past 6 months than the previous 3 years combined.
I've heard they're focusing on high income returns (over $400k) and those with Schedule C business income after getting that increased funding. Targeting where they think they'll recover the most unpaid taxes.
Just wanted to add my two cents as someone who's been running a small town transportation business for 3 years. Go with the LLC 100%. I started as a partnership and switched after a passenger threatened to sue when they tripped getting out of my car (nothing came of it, but scared me straight). The tax filing is identical either way (Form 1065), but the peace of mind knowing my house isn't on the line is worth the $100 annual fee my state charges. Also, banks and insurance companies took me more seriously as an LLC - got better rates on commercial insurance too.
That's really helpful to hear from someone who's already doing something similar! Did you find it complicated to switch from partnership to LLC after you'd already started? I'm worried about setting up something and then having to change it later.
It wasn't too bad switching from partnership to LLC, but definitely created some extra paperwork I could have avoided by starting with the LLC. I had to formally dissolve the partnership, file new paperwork for the LLC, get a new EIN, open new business bank accounts, and update all my insurance policies and client contracts. The whole process took about a month and cost around $500 including state fees and having my accountant update everything. Would have been much simpler to just start with the LLC from day one. The annual maintenance is super easy though - just a simple form and fee in my state. Your state might be different, so check your secretary of state's website for the specific requirements.
Has anyone used QuickBooks Self-Employed for a small driving service like this? Trying to figure out if it's worth the subscription vs just using spreadsheets for tracking mileage and expenses.
I use it for my handyman business and it's great for tracking mileage automatically. The app uses GPS to track your trips and you just swipe business vs personal. At the end of the year it calculates all your mileage deductions automatically. Definitely worth it if you're driving a lot for business.
Dylan Cooper
Hey, I've been using Taxport Convey for years. For the validation errors you're getting, there should be a "Review Exceptions" button on the main dashboard. Click that, then look for "Chapter 3 Exceptions" in the dropdown. From there, you can batch update all similar errors with the correct exemption code. For dividend payments under Chapter 3, if the recipient has provided a valid W-8BEN or W-8BEN-E claiming treaty benefits but no TIN, you generally have a 90-day grace period where you can still apply the treaty rate. After that, you may need to default to 30% withholding unless they qualify for another exemption. Also, make sure you're using the correct country code in the system - sometimes Taxport Convey will flag TIN issues if the country code doesn't match what's on the W-8.
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Zoe Stavros
ā¢Thanks for the specific guidance on Taxport Convey! I found the "Review Exceptions" option and it shows all 42 errors in one place. If I implement the 90-day grace period approach, will I need to go back and amend these later if we don't receive the TINs within 90 days?
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Dylan Cooper
ā¢Yes, if you don't receive the TINs within the 90-day period and you've applied treaty rates, you would technically need to file amended returns using the higher withholding rate (typically 30% for Chapter 3). However, there's an exception for certain passive income, including some types of dividends, where you may be able to continue applying treaty rates if you have other sufficient documentation. I would recommend documenting all your follow-up attempts to obtain the TINs. If you can show reasonable efforts to obtain the information, it can help if there's ever an IRS review of your filings.
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Sofia Ramirez
Just to add something useful - as someone who had to learn 1042/1042-S filing on the fly last year, I'd recommend downloading IRS Publication 515 and the 1042-S instructions. They're surprisingly helpful once you know what you're looking for. Specifically for your issue with Chapter 3 withholding, look at the section about "Withholding and Reporting Obligations" in Pub 515, around page 40-42. It outlines the scenarios where TINs are required vs. where you can proceed without them. The 1042-S instructions also have a table of exemption codes on page 25 that explains exactly when each one applies. Might save you some time vs. trying to piece it together from different websites.
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Dmitry Volkov
ā¢Publication 515 was super helpful when I was learning, but it's like 100+ pages. Any tips on finding the relevant sections quickly?
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