Selecting Planning Software and Tools

Financial planning software has evolved from basic spreadsheets to sophisticated platforms offering account aggregation, Monte Carlo simulations, and tax-optimized withdrawal strategies. Selecting the right tools requires understanding your planning complexity, technical comfort level, and budget. This guide examines the major software categories, compares critical features, and provides a framework for evaluation.

Software Categories and Primary Use Cases

Budgeting and Cash Flow Tools

These tools focus on tracking income and expenses, categorizing transactions, and helping users understand spending patterns.

Consumer Options:

• YNAB (You Need A Budget): $99/year, zero-based budgeting approach, manual transaction entry encouraged
• Mint (by Intuit): Free, ad-supported, automatic transaction categorization
• Copilot: $95/year (iOS/Mac only), clean interface, investment tracking included
• Monarch Money: $99/year, joint account features, goal tracking

Budgeting tools excel at the tactical level—understanding where money goes each month—but lack retirement projection and tax planning capabilities.

Comprehensive Financial Planning Platforms

Professional-grade platforms provide integrated planning across investments, retirement, taxes, and estate considerations.

Professional Platforms (typically advisor-facing):

• eMoney Advisor: Institutional pricing, extensive account aggregation, client portal
• RightCapital: $125–$250/month per advisor, strong tax planning module
• MoneyGuide/MoneyGuidePro: Institutional pricing, goal-based planning interface
• Orion Planning (formerly Advizr): Integrated with Orion portfolio management

Consumer/Prosumer Platforms:

• NewRetirement: $120–$240/year, detailed retirement modeling, DIY-focused
• ProjectionLab: $120/year, modern interface, scenario comparison
• Boldin (formerly Personal Capital Planning): Included with advisory service, limited standalone
• MaxiFi Planner: $109–$149/year, economics-based approach (consumption smoothing)

Investment Analysis Tools

Specialized tools for portfolio analysis and optimization:

• Morningstar Portfolio Manager: Free basic, $249/year premium with X-Ray analysis
• Portfolio Visualizer: Free basic, $228/year premium with advanced analytics
• Sharesight: $135–$270/year, strong for tracking cost basis and performance

Critical Feature Comparison

Account Aggregation

Account aggregation pulls balances and transactions from external financial institutions automatically.

Account aggregation quality directly impacts data accuracy. Broken connections require manual intervention and can lead to outdated planning assumptions.

Monte Carlo Simulation

Monte Carlo analysis runs thousands of randomized return scenarios to estimate probability of plan success.

Key Considerations:

• Number of trials: 1,000 minimum, 10,000 preferred
• Return assumptions: Historical vs. capital market expectations
• Correlation modeling: Do asset classes move realistically together?
• Sequence of returns: Are early retirement years weighted appropriately?
• Fee incorporation: Are investment costs deducted from returns?

Interpreting Results:

• 90%+ success rate: Potentially too conservative, may be underspending
• 75–90% success rate: Generally considered confident range
• 70–75% success rate: Acceptable with flexibility to adjust spending
• Below 70%: Plan adjustments recommended

Tax Projection and Optimization

Advanced platforms model tax implications of planning decisions:

• Roth conversion analysis: Projecting optimal conversion amounts across multiple years
• Tax-loss harvesting identification: Flagging positions with unrealized losses
• Asset location optimization: Placing investments in tax-appropriate account types
• Social Security timing: Modeling claiming age impact on lifetime taxes
• Required Minimum Distribution projections: Forecasting future RMD amounts and tax brackets

Reporting and Visualization

Effective tools present complex information clearly:

• Net worth tracking over time
• Goal progress dashboards
• Probability distribution charts (not just single-point estimates)
• Cash flow waterfalls showing income sources and expenses
• Tax bracket visualization across retirement years

Cost Analysis by User Type

Individual Investor (DIY approach)

High Net Worth Household ($1M+ investable)

Complexity increases with wealth: multiple account types, concentrated stock positions, stock options, rental properties, and estate considerations require more sophisticated tools.

Alternatively, engaging a fee-only advisor who provides software access through their planning platform may cost $3,000–$10,000 annually but includes professional interpretation and ongoing guidance.

Worked Example: Comparing Tools for $1M+ Household

Client Profile:

• David and Maria, both age 52
• Combined income: $285,000
• Investment assets: $1,340,000 (401k, IRA, Roth IRA, taxable brokerage)
• Real estate: Primary residence ($650,000 value, $180,000 mortgage)
• Goal: Retire at 62, maintain $120,000/year spending (today's dollars)
• Complexity factors: David has $200,000 in company stock (concentrated position), Maria has pension worth $35,000/year starting at 65

Tool Evaluation: Three Platforms Compared

Option A: NewRetirement Plus ($240/year)

Strengths:

• Detailed Social Security optimization modeling
• Roth conversion analysis with year-by-year recommendations
• Healthcare cost modeling through Medicare
• Handles pension income integration well

Limitations:

• Monte Carlo limited to 1,000 runs
• Concentrated stock position analysis basic
• No advisor collaboration features

Test Results:

• Plan success rate: 84% at $120,000 spending
• Recommended Roth conversions: $50,000/year ages 62–65
• Social Security claiming recommendation: Both delay to 70

Option B: ProjectionLab ($120/year)

Strengths:

• Modern, intuitive interface
• Excellent scenario comparison (side-by-side views)
• Strong cash flow visualization
• Responsive development team with frequent updates

Limitations:

• Account aggregation less robust than competitors
• Tax projections less detailed
• Pension modeling requires workarounds

Test Results:

• Plan success rate: 82% at $120,000 spending
• Scenario modeling showed retiring at 60 drops success to 71%
• Clear visualization of spending flexibility requirements

Option C: Advisor Platform (RightCapital via fee-only advisor)

Access Cost: Included with $4,500/year advisory fee (0.35% on $1.34M)

Strengths:

• 10,000-run Monte Carlo with detailed distribution analysis
• Tax bracket visualization across 30-year horizon
• Concentrated stock diversification modeling with tax impact
• Estate planning integration
• Professional interpretation of results

Limitations:

• Requires advisor engagement
• Higher total cost than DIY options

Test Results:

• Plan success rate: 86% at $120,000 spending
• Identified concentrated stock creates $45,000 potential tax liability if sold in single year
• Recommended 5-year diversification schedule saving $12,000 in taxes
• Pension integration accurate with COLA modeling

Evaluation Summary for David and Maria:

Recommendation: Given the concentrated stock position and pension complexity, engaging an advisor with RightCapital access provides value exceeding the fee differential. The tax savings from proper stock diversification sequencing ($12,000) covers multiple years of advisory fees.

For households without concentrated positions or pensions, NewRetirement Plus offers strong value for self-directed planners.

Implementation and Data Management

Initial Setup Process

1. Gather account information: Collect login credentials for all financial institutions
2. Establish aggregation connections: Link accounts, verify balances match statements
3. Input manual data: Real estate values, pension details, expected inheritances
4. Set assumptions: Inflation rate (2.5–3%), return expectations, spending adjustments
5. Run baseline scenario: Document current trajectory before making changes
6. Validate outputs: Compare projections against manual calculations for reasonableness

Ongoing Maintenance Schedule

Software Selection Checklist

Needs Assessment

• Define primary planning objectives (budgeting, retirement, tax optimization)
• Inventory current accounts and complexity factors
• Assess technical comfort level (DIY vs. guided)
• Establish annual budget for planning tools
• Determine need for advisor collaboration features

Feature Evaluation

• Verify account aggregation supports all financial institutions
• Confirm Monte Carlo methodology meets analytical needs
• Test tax projection capabilities against known scenarios
• Evaluate mobile access and interface usability
• Review data export options for portability

Trial and Testing

• Complete free trial or demo before purchasing
• Input actual financial data to test accuracy
• Compare outputs against manual calculations or advisor projections
• Test customer support responsiveness
• Read recent user reviews for reliability issues

Implementation

• Document all login credentials securely (password manager)
• Complete initial account linking and verify accuracy
• Input all manual data (real estate, pensions, Social Security estimates)
• Set realistic assumptions aligned with planning horizon
• Establish recurring calendar reminders for maintenance tasks

Ongoing Management

• Monitor aggregation connection health monthly
• Update assumptions when market conditions shift significantly
• Export data annually for backup purposes
• Reassess tool fit if planning complexity changes
• Compare to alternatives every 2–3 years as market evolves