Has anyone used one of those tax relief companies that advertise on the radio for an OIC? They claim they can settle for "pennies on the dollar" but I'm wondering if they're worth the fees they charge.

I'm currently in the middle of my OIC process (submitted about 4 months ago) and wanted to share what I've learned so far since you're just getting started. The biggest thing that's helped me is staying incredibly organized with a dedicated filing system for every single document. I created separate folders for initial application materials, correspondence with the IRS, financial documentation, and backup copies of everything. This has been a lifesaver when they've requested additional info. One thing I wish I'd known upfront - the IRS can take 6-24 months to process your offer, and during that time you MUST stay current on all new tax obligations. If you fall behind on estimated payments or filing requirements while your OIC is pending, they'll automatically reject your offer. I almost learned this the hard way. Also, don't let the anxiety get to you too much. Yes, it's intimidating dealing with the IRS directly, but if you're thorough with your documentation and honest about your financial situation, the process is more straightforward than it seems. The IRS agents I've spoken with have actually been professional and helpful when I've had questions. Good luck with your application! Feel free to ask if you have specific questions about the forms - I'm still fresh on all the details.

Has anyone noticed that tax software seems to get confused with inherited IRAs? I've used three different programs over the years and they ALL struggle with this scenario. I wish they would update their interfaces to make these questions clearer for situations like this!

I went through this exact same situation two years ago when my grandmother passed away and left me part of her IRA. The tax software confusion is real - I think the issue is that these programs are designed primarily for regular IRA distributions, not inherited ones. One thing that helped me was understanding that the "basis" question is really asking whether the original owner ever made contributions with money that was already taxed (after-tax contributions). Most traditional IRAs are funded entirely with pre-tax dollars, so there's usually no basis to worry about. The key is to look at your 1099-R form carefully. If Box 2a (taxable amount) equals Box 1 (gross distribution), then there's no basis and the entire amount is taxable. If Box 2a is less than Box 1, that might indicate some after-tax contributions were made. Since you confirmed with the financial institution that there were no after-tax contributions, you should be fine selecting "inherited IRA = Yes" and "basis = No" and then manually correcting any weird refund calculations the software produces. The important thing is that you report it as an inherited distribution so it's properly coded on your return.

One often overlooked issue with PTPs is how suspended losses affect your situation when selling. If you've received K-1s with losses that were suspended due to passive activity or at-risk rules, those suspended losses become deductible when you completely dispose of your interest. But for your scenario #2 (sell and rebuy), you technically haven't fully disposed of your interest for tax purposes if you rebuy within the same year. This means those suspended losses remain suspended despite the sale transaction. For the UBTI reporting on line 20V, death transfers can be especially confusing. Technically, the UBTI character passes through to the heir, but the step-up in basis can reduce future UBTI by giving you a higher basis to offset against UBTI income.

The relationship between capital accounts and UBTI/income allocation you mentioned is spot-on, and there's actually a specific reason for this. Partnerships are required to allocate items in accordance with partners' interests in the partnership, which is primarily determined by capital account balances under Section 704(b) regulations. When your capital account becomes more negative (through distributions exceeding your basis), your economic interest in future partnership income decreases proportionally. This is why you see lower per-unit income and UBTI when capital accounts are more negative - you're essentially getting a smaller slice of the same pie. For your death scenario question, there's an important distinction many people miss: while the step-up in basis applies to the fair market value of the PTP units, it doesn't directly reset your capital account with the partnership. The partnership maintains its own records of your capital account, which continues to reflect the cumulative income, losses, and distributions. However, for tax purposes, your new stepped-up basis can significantly reduce or eliminate the taxable gain when the inherited PTPs are eventually sold. One practical tip: if you're actively trading PTPs, keep detailed records of your holding periods and corresponding K-1 amounts. The partnerships' quarterly ownership snapshots mean your K-1 might not perfectly match your actual trading activity, and you'll need to be able to support any adjustments on your return.

Have you considered looking into other assistance programs instead of potentially risky tax situations? There are programs specifically designed to help people in your situation while waiting for disability approval. Many states have emergency assistance for families with newborns. Also, there are charities that help with car repairs for people who need transportation for medical reasons. These might be better options than depending on tax strategies that could cause problems later.

I understand you're in a tough financial situation, especially with a new baby and needing reliable transportation for medical appointments. However, I'd strongly encourage you to be very careful about the dependent claiming situation. From what you've described about your previous experience, it does sound like it may not have been entirely legitimate. The IRS dependent rules are strict - your sister would need to provide MORE than half of your total support for the entire year, and you'd need to meet the income requirements. Given that you mentioned having a baby recently, you might actually qualify for some additional tax credits yourself if you file your own return (like the Child Tax Credit), which could be more beneficial than being claimed as someone else's dependent. Before making any decisions, I'd really recommend getting professional advice. You could use one of the free tax preparation services available to low-income individuals, or even contact the IRS directly to understand your specific situation. The last thing you want is to face penalties or have to pay back benefits later when you're already struggling financially. Have you looked into local assistance programs for new parents or people awaiting disability approval? Many communities have emergency assistance funds specifically for situations like yours.

Have you considered asking the company to reclassify you as an employee instead of a contractor? If you were working regular hours at their location using their equipment, you might actually legally be an employee not a contractor. Companies sometimes misclassify workers as contractors to avoid paying employment taxes and benefits. It's actually pretty common in retail. If you were treated like a regular employee in practice, you might have been misclassified. Just something to consider if you're still working there or plan to in the future!

Just wanted to chime in as someone who went through this exact situation a couple years ago! I worked what felt like a regular retail job but got hit with a 1099-NEC at tax time. One thing I wish I'd known earlier - even though you have to file Schedule C and pay self-employment tax, you might qualify for the Qualified Business Income (QBI) deduction under Section 199A. This can give you up to a 20% deduction on your self-employment income, which helps offset some of that extra tax burden. Since your income was only $2,100, you should definitely qualify (the income limits are much higher). Most tax software will calculate this automatically once you enter your Schedule C info, but it's worth double-checking that it's being applied. Also, definitely track ANY expenses related to this work - even small things like work shirts, phone usage, or gas for work trips add up. I missed out on probably $200-300 in deductions my first year because I didn't think they mattered. Every little bit helps when you're dealing with that 15.3% self-employment tax on top of regular income tax!