Quickbooks Self-Employed has been a lifesaver for me with this exact problem. It lets you swipe left/right to categorize transactions as business or personal, and you can split transactions too if needed. Way easier than sorting through everything manually at tax time.

I went through this exact same situation with my consulting LLC last year! What really helped me was setting up a formal reimbursement system retroactively. I created expense reports for all the personal funds I'd used for business expenses, then had my LLC "reimburse" me by transferring money from the business account to my personal account. The key is maintaining that paper trail showing these were legitimate business expenses that you temporarily covered. I used a simple Excel template to document each expense with date, amount, vendor, business purpose, and which personal account I used. Then I'd do monthly reimbursements to myself. Your accountant will definitely appreciate that you've been tracking everything - that's honestly the hardest part. The fact that you have receipts and documentation puts you way ahead of most small business owners. Just make sure going forward you try to use business accounts when possible, but don't stress too much about the occasional personal payment as long as you document it properly.

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.

Pro tip: Go to your local tax office in person if you can. I did that last week and they helped me right away. Better than waiting on hold forever.

I went through this exact same thing last month! Had the same verification message for 7 weeks before it finally cleared. The key is definitely calling - I got through on my third try by calling right at 8 AM when they open. The rep told me that the verification process has been taking 6-8 weeks this year due to new fraud prevention measures, but once you hit that 6 week mark you can request an expedited review. They were actually really helpful and my refund was released 3 days after I called. Don't give up!

Another approach is to use a different tax software. I switched from TurboTax to TaxAct this year specifically because of issues with options reporting. TaxAct handled my 1256 contracts correctly and even has a specific section for mark-to-market positions that cross year boundaries. For your specific situation, you just need to enter the short put with positive numbers but in reverse order: the amount you received when opening the short position goes in the "proceeds" column, and the amount you paid to close it goes in the "cost" column. That way it properly calculates as a loss.

I actually had this exact issue with a /ES futures spread last year. The trick is to reverse how you think about the short position. For Form 6781: 1. For the short position: Put the amount you RECEIVED when opening the position as the PROCEEDS, and the amount you PAID to close it as the COST. 2. For the long position: Put the amount you PAID when opening as the COST, and the amount you RECEIVED when closing as the PROCEEDS. This way both will calculate correctly - the long showing a gain and the short showing a loss.

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.