Good questions.
Personal answers.

What are my tax-loss harvesting opportunities?

If I sell a position at a loss, what could I replace it with without triggering a wash sale?

I have large capital gains this year. What strategies could lower my tax bill before year-end?

What are my realized short-term and long-term gains and losses so far this year?

What's my taxable dividend income?

I'll upload my draft tax return next. Please wait for it, then compare the income and capital gains on it with what my accounts actually produced.

Would donating investments instead of cash change my tax outcome?

Does a donor-advised fund make sense for my situation?

How should I adjust my withholding or estimated tax payments so I'm not surprised at tax time?

Have I maximized my tax-saving opportunities this quarter?

What should I invest in my 401(k) given the investments I already own? I'll upload my plan's fund choices next. Please wait for the attachment, then suggest a mix that fits my whole portfolio and retirement timeline.

Am I on track to retire, and could I realistically retire early?

Run a Monte Carlo analysis of my retirement plan and show my odds of success.

Should I do a Roth conversion, and how much each year? Compare a few scenarios.

Should I contribute to a Roth or a traditional IRA?

What withdrawal order (taxable, pre-tax, Roth) keeps my taxes lowest in retirement?

Project my required minimum distributions and taxable retirement income for the next 10 years.

How will my retirement income and Roth conversions affect my Medicare premiums?

When should I claim Social Security?

What are the withdrawal rules for my inherited IRA?

Give me my current asset allocation across all accounts.

Show my current vs. target allocation across all accounts.

Help me get to my target allocation while minimizing taxes.

Am I too concentrated in any sector or single stock?

What's my exposure to technology, including holdings inside ETFs and mutual funds?

How much do I have invested in AI, including inside my funds? Should I diversify?

How has my portfolio performed against the S&P 500?

Which of my funds have high expense ratios, and what lower-cost alternatives could I consider?

Am I paying too much in advisory fees?

Which assets belong in my taxable, traditional and Roth accounts to minimize taxes?

What major news is moving my portfolio this week?

How could the latest tariff announcements affect my portfolio?

Did the latest inflation data affect my portfolio?

Are there any analyst rating changes affecting my top holdings?

Compare the performance of my two largest holdings.

I'll share a screenshot of a news story next. Please wait for it, then tell me how that scenario would affect my portfolio, including my exposure through funds, and which assumptions matter most.

Analyze my spending by category and show where my money goes each month.

What were my last five credit card payments?

Do I have enough cash in checking to cover my upcoming credit card payments?

I have cash sitting idle. Where should I put it, and how much should I keep as an emergency fund?

Show my total monthly income from dividends and interest, split by taxable and tax-advantaged accounts.

How has my credit card spending changed over the past month?

Draft a plan based on my accounts and goals.

I'm receiving an inheritance. How should I invest it given my goals and taxes?

How would a large one-time expense affect my cash flow and retirement plan?

How would taking a year off work affect my retirement plan?

How should I plan for my kids' education costs?

One stock makes up a large share of my portfolio. How should I diversify it with taxes in mind?

Review the financial plan from my advisor and tell me which assumptions look off.

Each day, cover the major news moving my portfolio.

Let me know if my allocation to tech goes above 25%.

Alert me when I have over $5,000 in idle cash.

Make sure there's always enough cash in my checking account to cover my credit card balances.

Every Friday, tell me the total balance across my checking, savings and credit card accounts.

Each week, alert me to positions with losses I could harvest, with a suggested replacement.

Alert me when my allocation drifts more than 5% from my target.

I'm expecting an insurance claim payout. Let me know when it arrives in one of my linked accounts.