Tax optimization comparison: PortfolioPilot vs Boldin/NewRetirement Tax modeling

According to the IRS, taxpayers can generally use up to $3,000 of net capital losses each year to offset ordinary income, and losses can be disallowed entirely if a substantially identical security is repurchased within 30 days under the wash-sale rule. The 3.8% Net Investment Income Tax may also apply once income crosses certain thresholds. Small choices in timing and lot selection can therefore have outsized, long-term tax effects.

Many investors assume “tax optimization” just means tax-loss harvesting (TLH). The bigger picture is broader: year-round hygiene in taxable accounts, plus multi-year planning around Roth conversions, RMDs, and Medicare IRMAA brackets. This article examines how PortfolioPilot and Boldin (formerly NewRetirement) approach tax optimization from different angles - ongoing, account-level tactics versus long-horizon tax modeling - so readers can see which workflow may fit their needs. 

Key Takeaways

• PortfolioPilot focuses on ongoing, account-level tax optimization (including TLH suggestions and wash-sale guardrails) delivered as monthly, personalized recommendations; it does not manage money or execute trades. 
• Boldin/NewRetirement centers on planning: multi-year tax modeling across income sources, Roth conversion exploration, and scenario analysis that can factor IRMAA and other constraints. Actions are user-driven. 
• TLH is only one lever; NIIT thresholds, bracket “fill-ups,” and Medicare premium brackets can matter as much as harvesting losses in a given year.
• Some investors may pair both approaches - planning multi-year moves in Boldin while using PortfolioPilot to spot near-term, portfolio-level tax opportunities.
  
  

Boldin/NewRetirement: Long-Horizon Tax Modeling

Many people want a forecast before they make moves. Boldin/NewRetirement lean into that planning need. Their resources and tools explain how potential Roth conversions, RMD timing, tax-gain harvesting, and Medicare IRMAA brackets may affect lifetime taxes. In practice, this means a user can model, “What if I convert $X at age 60?” or “What if I realize gains before a higher bracket year?” - then see tax-line impacts in the plan before acting. 

• Why it matters: Scenarios help avoid “surprise taxes.” For example, moving income across years can change exposure to the 3.8% NIIT or push modified AGI over IRMAA thresholds. Planning tools surface those cliffs early so a person can consider alternatives that better fit their risk tolerance and cash-flow needs. (So what? When decisions are complex - for example, multi-account households - pre-checking the tax map can reduce costly trial-and-error.)

PortfolioPilot: Ongoing, Account-Level Tax Optimization

PortfolioPilot is built for investors who want continuous prompts tied to their actual holdings - without handing over control. It analyzes connected accounts and then issues monthly, personalized recommendations that may include:

• Flagging tax-loss harvesting opportunities while noting wash-sale considerations.
• Reviewing asset allocation (which assets sit in taxable vs. tax-advantaged accounts) to help reduce projected tax drag over time.
• Highlighting the fee and distribution drag that may increase current-year taxes.
• Stress-testing decisions in the context of macro conditions and the user’s plan.

Why it matters: real portfolios drift, markets move, and distributions show up on their own schedule. Ongoing prompts can catch small, repeated savings opportunities that scenario planning alone might miss,  while still leaving the person in control of whether to act. (So what? For DIY investors who prefer to keep assets at their current brokers, “advice without custody” can be a practical fit.)

Why the Approach Difference Matters

Hypothetical: Consider a 45-year-old professional with a growing taxable portfolio and $275,000 in MAGI. A planner like Boldin could show that partial Roth conversions during an early-retirement gap reduce future RMDs and may avoid IRMAA surcharges in Medicare years. At the same time, PortfolioPilot might highlight harvestable losses during a volatile quarter, propose a similar-exposure ETF swap to avoid a wash sale, and suggest shifting a high-distribution fund into a tax-deferred account. Together, long-range modeling and day-to-day hygiene can work in tandem - one sets the roadmap; the other tunes the engine along the way. 

• So what? For many households, the most useful workflow isn’t either/or. It’s using a planner to decide when taxes should be paid, and a portfolio tool to decide how taxes are minimized this month - within IRS boundaries.

The comparison is based on publicly available information from each provider’s website as of 11/19/2025. Features, fees, and methodologies may change over time.