Scott & Courtney · Target: Nov 2027 sabbatical → 2028 permanent retirement · Ages 42
Run 2,000+ simulations against your Boldin cash flows. Test bucket strategy, spending flex, SS haircut scenarios. Upload new Boldin CSVs to refresh.
SimulationSize Roth conversions against the ACA cliff. Tracks dividends, muni interest, capital gains, and conversion headroom. Auto-switches HH4→HH3 at 2037.
Tax PlanningPlan which Miller lots to sell each year. 238 tax lots ranked by priority. Live MAGI tracking, 0% LTCG capacity, and sell plan builder. FIFO-friendly.
ExecutionMonth-by-month calendar, 50-year milestone roadmap, key thresholds, and year-by-year conversion/MAGI/cliff summary table. The master reference doc.
ReferenceSocial Security claiming strategy — breakeven, PV analysis, ACA impact, survivor benefit for Scott & Courtney.
PlanningIRS Uniform Lifetime Table RMDs from 2059–2090. Roth conversion opportunity panel shows tax savings from converting before 2059.
PlanningACA premium & subsidy tracker 2028–2051. Year-by-year cliff management, OOP estimates, Medicare transition in 2051.
Planning35-year federal tax projection. Roth conversion capacity, 0% LTCG harvest room, and bracket analysis for every year 2026–2060.
CalculatorLive balance sheet with asset allocation score, retirement milestones (25×/28.6×/33× expenses), and historical snapshot tracker.
Reference52-year income waterfall 2028–2079. Dividends, SS, portfolio draws, coverage ratio, and stacked-area canvas chart.
CalculatorSync Boldin PlannerPlus CSV export → updates Monte Carlo, Cash Flow, and all tools automatically. AI assistant paste mode included.
Data SyncLive YTD income vs ACA cliff. Know exactly how much Roth conversion and LTCG harvest room you have before hitting the cliff.
TaxPortfolio drift monitor vs 75/25 target. Tax-smart buy/sell action plan — tax-advantaged accounts first, then taxable.
PortfolioIRMAA thresholds for 2051 enrollment. Optimize 2049–2050 income to avoid surcharges. QCD strategy and Medigap comparison.
HealthcareDec 31 countdown with specific dollar amounts. Ordered checklist: Roth conversions, LTCG harvest, HSA max, charitable giving.
TaxSide-by-side comparison of 3 retirement scenarios. Change any assumption — retirement year, spending, returns, SS timing — see 40-year outcome.
SimulatorBeneficiary designation tracker, legal documents checklist, survivor financial plan. Estate readiness score with priority actions.
EstateBridge bucket CD/T-Bill/I-Bond ladder. 5-year income coverage plan with ACA MAGI impact analysis. I-Bond accumulation schedule.
IncomeMuni bond maturity strategy for BSMS (2027) and BSMR (2028). TEY calculator, bracket comparison, reinvestment options.
Bonds