One thing to consider - check if you closed out ALL positions before the year ended. If you rebought some positions in December that triggered wash sales but didn't sell them again before year end, those disallowed losses get carried over to the next year as part of your basis. I had a similar issue ($18K in wash sales) and found out I was holding positions on December 31st that had disallowed losses attached to them. A CPA probably can't help much with the current year taxes, but they might help you track which losses are deferred to next year. Also, were you trading in multiple accounts? That's another common way people get surprised by wash sales - selling at a loss in one account while buying in another (like a retirement account) within 30 days.

Have you thought about trying to sell some assets at a gain to balance out some of your income now? Might offset some of the tax hit.

Make sure you keep EVERYTHING related to this repayment! If you get audited (and unusual credits like this can sometimes trigger reviews), you want solid documentation. Save: - Email correspondence about the repayment - Bank statements showing the transfer - Any written agreements about the bonus repayment terms - Your original employment contract with the bonus terms I learned this the hard way when I had to repay some income and got audited two years later. Was a nightmare trying to find all the documentation.

Just want to add one more thing - double check if your state taxes need similar treatment! I had a repayment situation last year and completely forgot to handle the state tax portion. Had to file an amended state return which was a whole separate headache.

One thing nobody mentioned - check your transcript if you can access it online! The WMR tool is notoriously unreliable especially for PATH Act returns. My transcript showed codes 571/570 followed by 571/768/766 days before WMR updated. My DDD ended up being the cycle date + 6 days even though WMR still said processing.

My theory is the IRS intentionally gives vague info about PATH Act refunds to prevent people from calling all at once. I've gotten EITC for 5 years straight and every year is different. Last year my refund hit my acct on Feb 24th, the year before it was March 10th. Both times I filed in January. 🤷‍♀️ Just have to be patient even though it sucks when you need the money.

Someone I know tried the IRA-LLC structure for a different business (not blogging) and ran into major issues. The Self-Directed IRA custodian charged insane fees, and when the business generated over $1,000 in UBTI, they had to file Form 990-T which was a nightmare without professional help. Plus, their IRA had to pay the business fairly if they wanted to be involved personally. They ended up paying themselves a "fair market salary" from the IRA-owned LLC, which means that money was essentially taxed anyway (defeating some of the purpose), plus they had extra compliance costs. For a blog specifically, seems like WAY more headache than benefit unless you're planning to generate massive profits without personal involvement.

Just to add another consideration - what about SEO expenses and content creation costs? If the blog is in your IRA, you can't personally pay for things like hosting, domain registration, SEO tools, etc. All expenses MUST come from IRA funds. And if your blog needs capital for growth (better design, hiring writers, marketing), you're limited to what's in your IRA. You can't just add personal funds whenever needed without doing a formal IRA contribution (with all the normal limits).

Don't forget that the wash sale rule can seriously mess with your "simple" profit and loss calculation. If you sell a security at a loss and buy the same or "substantially identical" security within 30 days before or after the sale, you can't immediately claim that loss for tax purposes. I learned this the hard way last year trading tech stocks. Thought I had a $15k net loss only to discover that most of my losses were disallowed because I kept jumping in and out of the same stocks. The losses didn't disappear forever, but they got added to the cost basis of my replacement shares instead of offsetting my gains.

Another thing to consider is that if trading is your actual job/business rather than just investing, the tax treatment can be completely different. If you qualify as a "trader" in the eyes of the IRS (which has specific requirements about frequency, volume, and intent), you might be eligible for "trader tax status" and could potentially elect the Section 475 mark-to-market accounting method. This would treat all your trades as ordinary income/loss rather than capital gains/losses, bypassing the $3,000 capital loss limitation and wash sale rules. But this is a serious election with major implications and specific deadlines.