I'd recommend a slightly different approach that worked for me. Instead of selling the same stock in both accounts, consider selling the taxable account position for the tax loss, then immediately exchanging the IRA position for something different but similar (like a competitor in the same industry). This way you're not holding the "substantially identical" security in your IRA anymore, which should allow you to claim the tax loss. And since there are no tax consequences for selling at a loss in the IRA anyway, you're not giving anything up. Just make sure whatever you exchange into isn't considered "substantially identical" to the original security. This approach let me harvest the tax loss without being completely out of the market for 31 days.

This is a really common situation that catches a lot of people off guard! You're absolutely right to be concerned about the wash sale implications. Unfortunately, since you purchased the same stock in your IRA on January 15th (just 7 days after your taxable account purchase), selling the taxable position on February 18th would indeed trigger a disallowed wash sale. The IRS looks at all your accounts - including retirement accounts - when applying the wash sale rule. Here's what I'd suggest: If you want to claim the tax loss, you'll need to sell both positions and wait at least 31 days before repurchasing the same stock in either account. Since you mentioned the stock isn't recovering anyway, this might actually work in your favor from an investment perspective. One thing to keep in mind - your broker's 1099-B will likely NOT flag this as a wash sale because most brokers only track wash sales within the same account. It's your responsibility to identify and properly adjust for cross-account wash sales when filing your return. If you're looking to stay invested in the same sector, consider selling both positions and immediately buying a similar but not identical stock (like a competitor or sector ETF) to avoid being completely out of the market during the 31-day waiting period.

A quick tip if you do take this job - I make a deduction worksheet for all 1099 work. Track mileage between work sites (not commuting), any supplies you buy, portion of phone/internet if you use them for work, professional subscriptions, software, etc. Keep ALL receipts, take photos of them with your phone right away (they fade!). Also track any home office space if you do some work from home.

Just wanted to add another perspective here - I was in almost the exact same situation last year (required to work in their office, set schedule, but given a W9). After doing some research, I decided to take the job but immediately started documenting everything that showed I was really an employee, not a contractor. Things like: emails about required work hours, office policies I had to follow, equipment they provided, training materials, etc. After 6 months, I filed Form SS-8 with the IRS to get an official determination on my classification. The IRS ruled I was misclassified as a contractor and should have been an employee. Long story short - I got a refund for the extra self-employment taxes I paid, and my employer had to reclassify me and pay their portion of payroll taxes going forward. It was a bit of a process but totally worth it financially. If you take this job, document everything that shows they control how, when, and where you work. It could save you thousands later if you need to challenge the classification.

One thing nobody has mentioned is that Missouri has some specific state-level considerations for S-corps that differ from some other states. I'm a MO agent too, and our state taxes S-corps a bit differently than sole props. Make sure whoever you work with is familiar with MO specifically. Also, did your CPA mention anything about how the 20% QBI deduction factors into this decision? That's another big piece of the S-corp vs LLC analysis that might affect your choice.

Great point about Missouri-specific considerations! The QBI deduction interaction is crucial and often overlooked. For S-corps, the QBI deduction applies to your business income MINUS the W-2 wages you pay yourself. So if you're paying yourself a high salary (like that 70% some CPAs recommend), you're reducing the income eligible for the 20% QBI deduction. This creates an interesting balance - you want your salary high enough to avoid IRS scrutiny but not so high that you lose significant QBI benefits. In many cases, this actually supports the 50-60% salary range that others have mentioned here. Missouri also doesn't conform to federal S-corp elections automatically, so you need to make a separate state election. Plus MO has that franchise tax for S-corps that LLCs don't pay. These state-level costs should definitely factor into your breakeven analysis. I'd recommend running the numbers with both federal AND Missouri tax implications included. The total picture might be different than just looking at federal savings alone.

Just a heads up on something that surprised us during our C to S conversion last year - the Accumulated Adjustments Account (AAA) tracking became really important. After conversion, you'll need to carefully track AAA which is basically the post-conversion retained earnings that have already been taxed at the shareholder level. When you eventually distribute proceeds from property sales, the ordering rules for distributions can get tricky between AAA, accumulated E&P from the C corp days, and other sources. Our accountant messed this up initially and it almost resulted in some distributions being incorrectly taxed as dividends when they should have been tax-free returns of already-taxed income.

One thing I haven't seen mentioned yet is the potential impact of state taxes on this strategy. While the federal tax benefits of converting from C corp to S corp are well-documented, some states don't recognize S corp elections or have their own built-in gains taxes that could significantly impact your overall tax savings. For example, some states will continue to tax the entity as a C corporation even after federal S election, which could eliminate much of the benefit you're hoping to achieve. Other states have their own recognition periods or different rules for built-in gains. Given that you're dealing with real estate, you'll also want to consider whether your state has any special provisions for real estate held in corporate entities. Some states have additional taxes or fees for corporations holding real property that could affect your cost-benefit analysis. I'd strongly recommend getting state-specific advice from a tax professional familiar with your jurisdiction before moving forward with the conversion. The federal tax savings could be completely offset by unexpected state tax consequences.

Another option to consider is leasing instead of buying. My brother runs a transportation service for people with disabilities and he found that leasing the handicap vans gave him better tax advantages in his situation. The entire lease payment was deductible as a business expense (for the business use percentage), and he didn't have to worry about depreciation calculations. Just something to think about if you're not set on owning the vehicle outright!

Don't forget to look into potential ADA tax credits too! If your business qualifies as a "small business" under ADA guidelines (generally under $1 million in revenue or fewer than 30 employees), you might be eligible for the Disabled Access Credit, which could cover some of the cost of the accessibility modifications to the van. It's IRS Form 8826, and it can be taken in addition to your regular business deduction for the vehicle. It's specifically designed to help small businesses cover the costs of making services accessible to people with disabilities.