Multi-Year Tax Optimization & Scenario Planner
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Simulate Roth conversions, capital gains harvesting, and retirement withdrawals across multiple years to minimize lifetime taxes and maximize benefits.
Added Dec 7, 2025
12 signals
The Problem
Users face complex, interdependent tax decisions involving capital gains, retirement accounts, healthcare subsidies, and dependent taxation that require multi-year modeling. Current tax software is compliance-focused, not optimization-focused, and manual spreadsheet calculations are error-prone, time-consuming, and miss non-linear interactions between tax rules like ACA cliffs, kiddie tax phase-ins, and Roth conversion trade-offs.
Potential Solution
Detailed solution approach available for premium members.
Why Now?
Market timing analysis available for premium members.
Kiddie Tax for Child of Nonresident Alien Parents
Our son is a U.S. citizen (5 years old) and has some capital gains that are subject to U.S. tax. We live abroad, and both of us (the parents) are non-U.S. citizens who are **not** required to file U.S. tax returns. I understand that for the Kiddie Tax, any unearned income above $2,600 is normally taxed at the parents’ marginal tax rate. But since we don’t file U.S. taxes, we don’t have a U.S. taxable income or a U.S. tax rate. Does anyone know what tax rate applies in this situation? I’ve searched everywhere but can’t find a clear answer. Has anyone dealt with this before?
Net impact of Roth conversions with capital gains
I am looking into a Roth conversion for 2025. My income is under $30K, and my cap gains are over $100K. When I run scenarios, converting say $100K into a Roth fills up the 12% income bracket, but now it pushes all of my capital gains from a 0% bracket into 15%. So my effective marginal tax rate is in the 22-24% range. Am I doing this right? And is there a strategy to generate cash for living expenses but keep my capital gains lower?
Capital Gains Harvesting 21 year old
I am in a unique situation, I recieved an inheritance from my grandpa of $150,000 in cash. I then invested this money in a brokerage account and it has gown to $168,000 as of now, all of the gains in the account are now long term capital gains. I am only 21 years old and work a part time job. I am familiar with the concept of loss harvesting, I am actually wondering if i can do the opposite. Since my taxable income for 2025 will be roughly $20,000 and the 0% cap gains rate is up to $48,350 can I harvest the $18,000 in gains in the account and effectively give myself a free step up in basis? And how much do we think I can do? In my head I imagine $48,350 - 20k income so up to like $18,350 in gains? Is this at all correct?
Seeking advice - generating enough income to use under the 400% FPL subsidy cliff for the ACA
56 single male, no dependents. I would like to retire, and use my after tax brokerages and stock positions (600k) to fund my roughy $55k yearly spend. I have a 401k with 1.8 million, and a cash pension of $150k but would rather allow that to continue to grow without touching it (yes, I know about the rule of 55). My question is, given that I would be paying virtually $0 in long term capital gains I will show virtually no income and the way the system works in my state, that would put me in the Medicaid bucket. Any advice as to how I could generate enough income to surpass the Medicaid level and allow me to enroll in an ACA plan? Looking for options other than taking a part time job.
Where’s the line between legal tax planning and tax evasion?
My manager always says: “It’s not tax evasion if it’s legal.” For those of you in tax/accounting, where do you personally draw the line between **aggressive but legal tax planning** and **unacceptable/abusive** behavior? I’m not asking for personal schemes, just curious how people think about the gray area in practice. If anyone here works with high-net-worth clients or billionaires, hearing what they usually do in practice would also be really interesting.
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