2 What kind of side gig do you have? I found that the complexity of my taxes really depended on what type of self-employment I was doing. When I was just doing simple freelance writing, TaxAct's regular version was fine without any upgrades. But when I started an Etsy shop with inventory and supplies to track, I definitely needed more help.

I used TaxAct Xpert Assist last year when I had a similar situation - W-2 income plus freelance work and a cross-state move. The upgrade was definitely worth it for me. The live agent helped me identify several deductions I hadn't considered, like the moving expense deduction (which I thought was eliminated but still applies in certain situations) and helped me properly allocate my freelance income between states. They also walked me through estimated quarterly payments for this year, which saved me from underpayment penalties. For your income level and complexity, I'd say it's worth the upgrade cost. The agent I spoke with was knowledgeable and patient, and I felt like I got personalized advice rather than generic responses. Just make sure to have all your documents ready when you call - the more organized you are, the better they can help you maximize your deductions. One tip: schedule your call during off-peak hours if possible. I called on a weekday morning and got through quickly with plenty of time to discuss everything thoroughly.

I went through this exact scenario with two different clients in the past year, so I completely understand your stress! Here's what I learned from those experiences: First, the rejection of your e-filed extension is actually normal when there's a disconnect between your filed return and the IRS's system records. This doesn't necessarily mean your S election was denied - it's more likely that their systems just haven't synced up yet. For immediate protection, definitely mail Form 7004 via certified mail and mark it as an S corporation extension. Include a brief cover letter explaining that you have a pending S election under review. This creates documentation of your good faith effort to comply. Regarding your short tax year dates (9/1/22-12/31/22), those were absolutely correct if that's when business operations actually began. Don't second-guess yourself on this - the IRS expects the first tax year to reflect actual business activity dates. One thing I'd recommend is getting a Power of Attorney (Form 2848) on file if you don't already have one. This will make it much easier when you call the IRS to check on the election status, as they can speak directly with you about your client's account. The good news is that even if there are delays, you can usually get retroactive relief if you can demonstrate reasonable cause for the late filing. Keep detailed records of all your submission attempts and communications with the IRS.

I've been through this exact situation multiple times with clients, and I want to reassure you that this is more common than you think, especially with the IRS processing delays we've seen lately. Here's my step-by-step recommendation based on what's worked for my clients: 1. **Immediate action**: Mail Form 7004 via certified mail TODAY if you haven't already. Check the S-corp box and include a brief statement that the S election is pending IRS processing. This protects your client from penalties. 2. **Verify election status**: Call the Business & Specialty Tax Line at 800-829-4933 first thing in the morning. Navigate to the Form 2553 department specifically. Have your client's EIN, business name, and the date you submitted the election ready. 3. **Don't panic about the dates**: Your 9/1/22-12/31/22 short year was absolutely correct since that's when operations began. This won't cause approval issues. 4. **System disconnect is normal**: The e-filing rejection usually means their systems haven't synced, not that your election was denied. I've had clients where the election was approved weeks before the e-filing system recognized it. The key is getting confirmation of your election status first, then you'll know exactly how to proceed. Most of these situations resolve favorably - it's just the waiting and uncertainty that's stressful. Keep detailed records of all your calls and submissions for your files. You've got this! Let us know what you find out when you call.

Has anyone considered the $20k might trigger some kind of reporting? I thought banks had to report large deposits?

I did something very similar with my brother last year for a Chase bonus. The key thing is to make sure your dad understands he'll need to report the $300 as income on his tax return - the bank will send him a 1099-INT form. One thing I learned is to keep good records of the initial transfer and the payback. I took screenshots of both transactions and kept them with my tax documents, just in case there were ever any questions. The IRS sees lots of these temporary family arrangements for bank bonuses, so as long as everything is reported properly, you should be fine. Also, make sure to read the bank's terms carefully. Some specify the money needs to stay in the account for a certain period after the bonus posts before you can withdraw it without penalty.

This is actually pretty common during peak filing season! The IRS has different systems for acceptance vs processing. When TaxAct said "approved," they meant your return passed the initial validation checks and was accepted into the IRS queue. But the actual processing (where it shows up in their records) can take 1-3 weeks. The verification letter you received was likely requested by a third party - maybe for a loan application, government benefits, or background check? These are often automatically generated when someone needs proof of your filing status. Since you filed on Feb 12th and the verification was requested on Feb 16th, there just wasn't enough time for your return to fully process yet. I'd definitely call that 800 number to clarify, but don't stress too much. Your return is probably just sitting in their processing queue. The state refund hitting your account is actually a good sign - it means your federal return info was transmitted properly.

This exact same thing happened to my brother last month! The key thing to understand is that "acceptance" and "processing" are two completely different stages. TaxAct showing approval just means your return made it through the electronic filing gateway without errors - it doesn't mean the IRS has actually processed it yet. The verification of non-filing letter is usually triggered when someone (like a lender, school, or government agency) requests proof that you haven't filed taxes for a specific period. Since you filed on Feb 12th and they checked on Feb 16th, your return was probably still in the processing queue. My brother called that same 800 number and they confirmed his return was "in process" even though the verification letter said they had no record. Took about 10 days total from filing to showing up in their system. The rep told him these letters are automatically generated and don't account for recent filings still being processed. Definitely call them, but you're probably fine! The fact that your state refund already came through is actually a really good indicator that everything went through correctly on the federal side too.

Important point that hasn't been mentioned yet - the timing of UBIT tax payments. If your expected UBIT tax will exceed $500 for the year, your IRA must make quarterly estimated tax payments using Form 990-W. Missing these payments can result in penalties, and many self-directed IRA investors don't realize this until it's too late. I learned this the hard way last year and got hit with penalties.

One thing I wish I had known before investing my IRA in a real estate syndication - make sure to get clarity on exactly how the sponsor will handle K-1 distribution timing. My syndication was supposed to issue K-1s by March 15th, but they were delayed until mid-April, which made it impossible to file my IRA's Form 990-T by the deadline. This created a cascade of problems because my custodian charges a $150 late filing fee, plus I had to file for an extension and pay penalties to the IRS. The delay also meant I couldn't accurately project my UBIT liability for the following year's estimated payments. Another consideration - some syndications have "side letters" or management agreements that could potentially create prohibited transaction issues if there are any relationships between the sponsor and other service providers. I learned to specifically ask sponsors about any affiliated entities providing services to the LLC, as this could complicate the prohibited transaction analysis for IRA investors. The due diligence process for IRA investments in syndications is much more complex than regular investing, but the returns can justify the extra effort if you do your homework properly.