We hadn't considered switching from Roth to traditional for his contributions. That's actually a really good point about the immediate tax savings. Do you think the long-term benefit of Roth (tax-free growth) outweighs the current tax deduction we'd get from traditional? I'm torn because I know Roth is often recommended, but our current tax situation is stressing me out.

Whether Roth or traditional is better really depends on your current tax bracket versus what you expect in retirement. At your income level (around $214k combined), you're likely in the 24% or 32% federal bracket. If you expect to be in a lower bracket in retirement, traditional contributions make more mathematical sense now. Many financial advisors recommend a mix of both for tax diversity in retirement. You could consider having one spouse do traditional and one do Roth, or splitting contributions. Given your current tax stress, moving at least some money to traditional contributions would give you immediate relief. You can always adjust your strategy in future years as your income and tax situation changes.

The "married but withhold at higher single rate" option doesn't exist on the new W-4 forms anymore. They redesigned them in 2020. Now you have to check a box in Step 2 for "multiple jobs" or do more complicated calculations. The new forms are even more confusing imo.

That's a great point about owner-manager taxation! I've had limited exposure to this through some of the trust work, but haven't seen the full picture of how it integrates with corporate planning. Is there a particular industry you think would give the best exposure to these concepts during a short secondment?

Professional services firms (doctors, lawyers, dentists) typically offer the richest learning experience for owner-manager taxation because they have more flexibility in their structures than capital-intensive businesses. They often have complex structures with holding companies, family trusts, and professional corporations all working together. Real estate is another good sector if you want to see how capital gains planning works in practice. The strategies used for property developers versus long-term holders are quite different, and you'll learn a lot about timing strategies for triggering gains or losses.

Totally agree with this distinction! I'd also add that if you're someone who likes definitive answers, tax preparation might be more satisfying. Planning work involves a lot more gray areas where you're dealing with probabilities rather than certainties.

This is what scares me about these situations. Did your sister have any idea the preparer was doing shady stuff? Like did she sign the return without reviewing it, or did the preparer hide what they were doing?

She had some suspicions when her refund was so much higher than usual, but the preparer assured her everything was "industry standard" and "completely legal tax strategies." My sister didn't understand all the tax jargon and forms, so she trusted the "professional." The preparer had her sign the final return without really explaining the details, and my sister didn't carefully review what was filed. The reality is that most people don't understand tax forms well enough to catch these issues, which is exactly what these shady preparers count on. When the audit came, the preparer's phone was disconnected and the office was empty.

I tried this approach with a similar situation. I asked the preparer to explain specifically what deductions she was claiming and why I qualified. She got super defensive and vague, saying things like "I have 20 years of experience" and "I know what I'm doing." When I insisted on seeing the actual forms before filing, she tried to rush me through signing. Huge red flag.

That definitely sounds suspicious! You're right that a legitimate tax professional should be able to clearly explain their strategy without getting defensive. I guess the best approach is to ask specific questions and expect specific answers. I still think there's a small chance this person just knows the tax code really well and finds legitimate deductions others miss, but the defensiveness you described would make me walk away too. Thanks for sharing your experience!

That's a really helpful perspective I hadn't considered. Our son is financially responsible, but this might be valuable info for friends in different situations. Does a Spendthrift Trust still avoid probate like a regular living trust?

Yes, a properly structured Spendthrift Trust still avoids probate just like a regular living trust would. The main difference is just the added protection and control over how and when distributions are made. Many people don't realize that these specialized trusts can be created for reasons other than disability - sometimes it's just about protecting someone from their own financial decisions or from predatory relationships. The important thing is that they offer the same probate-avoidance benefits while adding an extra layer of protection.

Did adding your daughter trigger a property tax reassessment in your county? In our area, parent-child transfers get an exclusion from reassessment, but only if you file the right paperwork within a certain timeframe.

No reassessment in my case, but that's because I filed for the parent-child exclusion with our county assessor's office. You have to file Form BOE-58-AH (at least in our county) within 3 years of the transfer to claim the exclusion. If you miss that window, they can reassess the property to current market value, which would have increased my property taxes by about 400% given how long I've owned my home! Definitely check your local rules and don't miss any deadlines.

Do you know if before/after school programs count as childcare expenses? My kids are in elementary school but I pay for after-school care until I get off work. My tax software is giving me contradictory information about whether this qualifies.

Yes, before/after school programs definitely count as qualifying childcare expenses as long as they allow you to work or look for work. The IRS is pretty clear on this - any care provided for children under 13 that enables you to work or actively search for work qualifies. The key is that the primary purpose of the program must be childcare, not education. Most standard before/after school programs fall into this category. Summer day camps can also qualify, but overnight camps don't. Make sure you get the tax ID or SSN of the provider, as you'll need to include that on Form 2441.

Thank you! This worked for me too. When I went to the form view, I saw TurboTax had somehow entered part of my childcare expenses in the wrong field. It was counting some of my expenses as "dependent care benefits" from an employer (which I don't have). Once I zeroed out that field and put everything under the actual expenses, it calculated correctly to $600. Thanks everyone for the help! Saved me from either overpaying for the "expert" review or submitting an incorrect return.

Glad it worked for you! I've found that looking at the actual forms is always the best way to catch these errors. TurboTax and similar software try to make things "easy" by hiding the forms behind their interview questions, but sometimes that just creates confusion. For anyone else with this issue, another thing to check is that your care provider information is entered correctly. If the provider's tax ID is missing or formatted incorrectly, some tax software will reduce the credit amount without clearly explaining why.