Just a warning from personal experience - if you're using TurboTax, it sometimes gets confused with multiple Schedule Cs, especially when they're related entities. Last year it kept thinking I was trying to report the same business twice. I ended up having to call their support line. Might want to consider using a tax pro the first year you set this up just to make sure everything's being reported correctly.

I've been through this exact scenario with my consulting LLC that spawned a separate tech services division. You're absolutely right about the tax treatment - everything flows through to your personal return since both LLCs are disregarded entities. One practical tip: when you set up that dedicated credit card for the subsidiary, consider getting a business card specifically in the subsidiary LLC's name once it's established. This makes expense tracking much cleaner and helps maintain the "corporate veil" between entities. Until then, your reimbursement approach is perfectly fine. Also, don't overthink the EIN situation. I got separate EINs for each of my LLCs even though I could have used my SSN, and it's made banking, vendor relationships, and general business operations much smoother. The paperwork is minimal and it's free to get an EIN directly from the IRS website. For bookkeeping, I second the recommendation about using classes or locations in QuickBooks if you go the single-file route. Just make sure your chart of accounts is detailed enough to easily separate expenses by entity at year-end. The key is being able to generate clean financial statements for each business independently, even if you're filing them together on your tax return.

I think everyone is overcomplicating this. The Code R on 1099-R literally just means "Recharacterized IRA contribution." The IRS knows exactly what this is. You report it on your 2023 return (the year of the 1099-R) and move on. Box 2a is $0 because there's no taxable amount - it's just moving money from one type of IRA to another. TurboTax is suggesting an amendment because their software is designed to be extra cautious. But unless you're eligible for a traditional IRA deduction you didn't claim (which sounds unlikely given you have a 401k), there's no benefit to amending.

Just to add some clarity from the technical side - when you recharacterized your Roth IRA contribution to traditional before filing your 2022 return, you essentially treated it as if the contribution was always made to the traditional IRA. The 1099-R with Code R in 2023 is just the custodian's way of reporting that recharacterization transaction to the IRS. Since you did this before filing your 2022 taxes, your original return should have reflected the traditional IRA contribution (either as deductible or non-deductible depending on your income and workplace plan). The key question now is whether you properly reported that traditional IRA contribution on your 2022 return. If you didn't report it at all, you might need to file Form 8606 for non-deductible contributions to establish basis, but that's separate from the 1099-R Code R issue. The 1099-R itself goes on your 2023 return with no additional tax owed since box 2a shows $0 taxable amount.

I've been both 1099 and S Corp over my 15-year consulting career, and here's my practical take: at $675k, the S Corp advantage is massive, BUT remember you're trading simplicity for tax savings. With an S Corp you'll need: - Regular payroll processing - Workers comp insurance in many states - More complex bookkeeping - Corporate formalities (minutes, etc.) - Separate business banking - Annual state fees and reports The tax savings easily justify this complexity at your income level, but be prepared for about 5-10 hours/month of additional administrative work unless you outsource it all (which eats into your savings). One final note: many banks offer better business lending terms to established entities vs. sole proprietors. This became hugely valuable when I wanted to purchase commercial property for my business.

At your income level, you're definitely leaving substantial money on the table by staying as a 1099 contractor. I made the switch to S Corp about 3 years ago when my consulting income hit similar levels, and the tax savings have been significant. Here's what I wish someone had told me upfront: the "reasonable salary" determination is crucial and can make or break your tax strategy. I researched comparable salaries in my field extensively and settled on about 35% of my total profit as salary. This saved me roughly $45k annually in self-employment taxes while staying well within IRS guidelines. One thing that surprised me was how much the business entity opened up additional deduction opportunities beyond just the payroll tax savings. Business meals, travel, equipment purchases, and even my home office became much more defensible as legitimate business expenses. The administrative burden is real though - I spend about 2-3 hours monthly on corporate maintenance tasks, plus the added cost of payroll processing and a good business accountant. But when you're saving tens of thousands annually, those costs are easily justified. My advice: start the process now to be ready for next tax year, and definitely consult with a tax professional who specializes in S Corps. The setup cost will pay for itself many times over at your income level.

You're absolutely right to be concerned about the marriage penalty - it's a real issue that affects many couples, especially when one person qualifies for Head of Household status. A few things to consider beyond just the standard deduction difference: 1. **Income-based credit phaseouts**: When you combine incomes, you might lose eligibility for credits like the Earned Income Tax Credit or Child Tax Credit that you currently qualify for. 2. **Tax bracket considerations**: Your combined income might push you into higher tax brackets faster than if you filed separately. 3. **Married Filing Separately option**: While you'd lose some benefits, this might reduce the penalty in your specific situation. You'd need to run the numbers both ways. 4. **Timing strategy**: Since marital status is determined on December 31st, you could potentially delay your wedding until January to get one more year of favorable tax treatment. I'd strongly recommend getting a professional tax projection done with your actual numbers before making this decision. The rough calculations can be misleading because there are so many variables that interact with each other. A tax professional can show you exactly what the impact would be and might identify strategies to minimize it. Don't let taxes be the only factor, but definitely factor them into your overall financial planning for marriage!

I went through this exact situation two years ago! As a single mom filing Head of Household, I was terrified about the marriage penalty. What I discovered is that while yes, there IS a penalty in terms of standard deductions and tax brackets, the real-world impact depends heavily on your specific income levels and deductions. Here's what helped me: I tracked down every possible deduction and credit change that would happen. For example, if your boyfriend has student loan interest or other deductions that you can't currently claim, those might help offset some of the penalty when you file jointly. Also, look into whether your combined income would still qualify for credits like the Child Tax Credit - sometimes the income limits are higher for married couples. The timing suggestion others mentioned is huge. We actually moved our wedding from December to February specifically to get one more year of Head of Household status. That one decision saved us over $4,000. Bottom line: run the actual numbers with a tax professional who can look at your complete picture. The marriage penalty is real, but there are often ways to minimize it that aren't obvious from just looking at standard deductions.

I would perhaps suggest approaching this situation with caution. In several cases I've observed, taxpayers who received checks at old addresses experienced subsequent identity verification holds on their accounts in following years. The Department may, in some instances, flag these accounts for additional scrutiny during the next filing season, particularly if the check was returned undeliverable. This could potentially delay future refunds by approximately 60-90 days while identity verification processes are completed.

This is incredibly frustrating but unfortunately very common with PA state refunds. I experienced this exact same issue last year - filed with direct deposit selected and current address, but they sent a paper check to my old address from 2021. What I learned from dealing with PA DOR is that their system has a major flaw: if there's ANY discrepancy between your current filing address and what they have in their legacy database, they automatically override your direct deposit election and mail a paper check to whatever address they have on file - which could be years old. The key steps that actually worked for me: 1. Call PA DOR immediately (yes, the wait times are brutal) 2. Request a refund trace - they'll give you a reference number 3. File Form REV-763 to officially update your address 4. If the check hasn't been cashed, they can usually stop payment and reissue Pro tip: Set up mail forwarding with USPS as a backup, but don't rely on it alone since tax documents sometimes can't be forwarded. The whole process took me about 6 weeks to resolve, but I did eventually get my refund. Pennsylvania really needs to fix this system - it's affecting way too many taxpayers every year.