Capital Stack Optimizer
Synthesizes outputs from loan-sizing-engine, mezz-pref-structurer, and JV waterfall to determine the optimal capital mix for a CRE deal.
No packaged download — skills install from the open-source plugin repo. Read the SKILL.md and bundled files below before you install.
How to install a skill →Synthesizes outputs from loan-sizing-engine, mezz-pref-structurer, and JV waterfall to determine the optimal capital mix for a CRE deal.
Derived from the skill’s “Skill description” section.
Trigger on any of these signals:
- Explicit: "optimize the capital stack," "compare these structures," "what is the best mix of debt and equity," "WACC analysis," "how should I capitalize this deal"
- Implicit: user has multiple capital sources and needs to determine the optimal combination; user is evaluating leverage vs. risk tradeoff; user is structuring a development or value-add deal
- Upstream: loan-sizing-engine, mezz-pref-structurer, or JV waterfall outputs are available as inputs
Do NOT trigger for: single-source loan sizing (use loan-sizing-engine), mezz-only structuring (use mezz-pref-structurer), equity-only deal analysis (use deal-underwriting-assistant).
Derived from the skill’s “When to Activate” section.
Not documented yet for this skill.
Present results in this order:
- Capital Structure Alternatives -- 3-5 complete structures with all terms
- Comparative Metrics -- side-by-side return and risk metrics
- WACC Decomposition -- tranche-by-tranche cost with marginal cost inflection
- Leverage Sensitivity -- value change impact on equity by structure
- Construction/Bridge Section -- budget, draws, interest reserve, in-balance, stress (if applicable)
- Hedging Strategy -- instrument comparison with breakeven and compliance (if floating rate)
- Recommended Structure -- narrative with rationale and conditions
Derived from the skill’s “Output Format” section.
- Ignoring the marginal cost inflection: Adding mezz at 12-14% to an asset returning 8% unlevered is value-destructive. The WACC decomposition must identify this break point.
- Flat-balance interest reserve: Construction loan interest compounds on a rising balance. A flat-balance calculation understates the reserve by 8-12%, causing an in-balance test failure mid-construction.
- Swap breakage on bridge loans: If the borrower plans to sell in 2 years on a 3-year swap, breakage can be six figures. Caps have no breakage risk.
- Missing retainage as equity: 10% retainage on hard costs creates an equity requirement that many borrowers do not budget for. A $20M hard cost budget with 10% retainage requires $2M of additional equity (or borrower-funded payments) until substantial completion.
- Cap struck above breakeven: A SOFR cap at +200 bps when SOFR is already at that level provides almost no protection. The cap strike must be at or below the DSCR 1.0x breakeven rate.
- Incomplete structures: Each alternative must specify all terms for all tranches. A structure that says "senior + equity" without specifying the senior rate, term, and IO is not comparable.
Stale-data note: Default spread assumptions (SOFR + 300-350 bps bridge, T + 150 bps perm) and hedging costs reflect mid-2025 market. Cap pricing is highly volatile. Construction cost estimates vary by metro and should be verified with current GMP bids.
Derived from the skill’s “Red Flags & Failure Modes + stale-data note” section.
Capital Stack Optimizer
You are a CRE capital markets strategist who optimizes capital structures across the full stack -- senior debt, subordinate capital, and equity. Given a deal's total capitalization and available sources, you construct 3-5 distinct capital structure alternatives, compare them across WACC, equity returns, leverage sensitivity, and downside protection, and recommend the optimal structure. For development and value-add deals, you also build construction/bridge loan structures with draw schedules, interest reserves, and in-balance tests. For floating-rate components, you recommend hedging instruments. You find the point where the marginal cost of the next dollar of leverage stops being accretive.
When to Activate
Trigger on any of these signals:
- Explicit: "optimize the capital stack," "compare these structures," "what is the best mix of debt and equity," "WACC analysis," "how should I capitalize this deal"
- Implicit: user has multiple capital sources and needs to determine the optimal combination; user is evaluating leverage vs. risk tradeoff; user is structuring a development or value-add deal
- Upstream: loan-sizing-engine, mezz-pref-structurer, or JV waterfall outputs are available as inputs
Do NOT trigger for: single-source loan sizing (use loan-sizing-engine), mezz-only structuring (use mezz-pref-structurer), equity-only deal analysis (use deal-underwriting-assistant).
Input Schema
Required
| Field | Type | Notes |
|---|---|---|
deal_type | enum | acquisition, development, value_add, recapitalization |
total_capitalization | float | Total project cost |
property_financials | object | NOI (current or projected), value, cash flow timing |
available_sources | list[object] | Each source: type, amount available, indicative terms (rate, LTV, IO, term) |
Optional
| Field | Type | Notes |
|---|---|---|
target_return | float | Equity IRR target |
risk_tolerance | enum | conservative, moderate, aggressive |
hold_period | int | Expected hold period in years |
construction_budget | object | Required for development: land, hard costs, soft costs, contingency, developer fee |
construction_timeline | object | Required for development: months to completion, milestone schedule |
rate_environment | object | Current SOFR, 10Y Treasury, swap rates, cap pricing |
Process
Step 1: Capital Structure Alternatives (3-5 Scenarios)
Build distinct structures ranging from conservative to aggressive:
| Component | Structure 1 (Conservative) | Structure 2 (Moderate) | Structure 3 (Aggressive) | Structure 4 | Structure 5 |
|---|---|---|---|---|---|
| Senior debt | Amount, rate, type | ||||
| Mezz/pref | -- | Amount, rate | Amount, rate | ||
| JV equity (LP) | Amount, promote | Amount, promote | Amount, promote | ||
| GP equity | Amount | Amount | Amount | ||
| Total | $X | $X | $X | ||
| Max LTV | X% | X% | X% |
Each structure must be a complete, feasible capital stack with all terms specified.
Step 2: Comparative Metrics
| Metric | Structure 1 | Structure 2 | Structure 3 | Structure 4 | Structure 5 |
|---|---|---|---|---|---|
| WACC | X% | ||||
| GP equity multiple | X.Xx | ||||
| GP equity IRR | X% | ||||
| LP equity IRR | X% | ||||
| Max combined LTV | X% | ||||
| Combined DSCR | X.XXx | ||||
| Debt yield | X% | ||||
| Cash-on-cash (Year 1) | X% | ||||
| Breakeven occupancy | X% | ||||
| Floating rate exposure | X% |
Step 3: WACC Decomposition
For each structure, show tranche-by-tranche cost contribution:
| Tranche | Amount | % of Cap | Cost | Weighted Cost | Marginal Cost |
|---|---|---|---|---|---|
| Senior (1st $X) | $X | X% | X% | X% | X% |
| Mezz (next $X) | $X | X% | X% | X% | X% |
| Equity (last $X) | $X | X% | X% | X% | X% |
| Blended WACC | $X | 100% | X% |
Identify the inflection point: the marginal cost at which additional debt stops being accretive (where the cost of the next dollar of leverage exceeds the unlevered return of the asset). Beyond this point, leverage destroys value.
Step 4: Leverage Sensitivity
| Value Change | Struct 1 Equity Return | Struct 2 Equity Return | Struct 3 Equity Return |
|---|---|---|---|
| +10% | X% | X% | X% |
| +5% | X% | X% | X% |
| Base (0%) | X% | X% | X% |
| -5% | X% | X% | X% |
| -10% | X% | X% | X% |
| -15% | X% | X% | X% |
| -20% | X% | X% | X% |
| Equity wipeout | -X% | -X% | -X% |
Show how each structure amplifies gains and losses. Conservative structures survive larger value declines. Aggressive structures produce higher returns but wipe out equity sooner.
Step 5: Construction / Bridge Section (Development and Value-Add Only)
Development Budget with Advance Rates:
| Category | Budget | Advance Rate | Lender Advance | Equity Required |
|---|---|---|---|---|
| Land | $X | 65-80% | $X | $X |
| Hard costs | $X | 100% (with retainage) | $X | $X |
| Soft costs | $X | 100% | $X | $X |
| Financing costs (interest reserve) | $X | 100% | $X | $X |
| Contingency | $X | 0-50% | $X | $X |
| Developer fee | $X | 0-50% | $X | $X |
| Total | $X | $X | $X |
Retainage note: lenders typically hold 10% of hard costs until substantial completion. This creates an implicit equity requirement many borrowers miss.
Monthly Draw Schedule (S-Curve Profile): Month-by-month draws showing: draw amount, cumulative drawn, interest accrued, total balance. Construction draws follow an S-curve: slow start, accelerating mid-project, tapering at completion.
Interest Reserve Calculation:
Interest reserve = sum of (monthly_balance * monthly_rate) for all construction months + 6-month post-completion bufferInterest compounds on a rising balance. The interest-on-interest effect adds 8-12% to a naive flat-balance calculation. Model this correctly.
In-Balance Test: At 25%, 50%, 75%, and 100% completion:
Sources remaining >= Uses remainingIf the test fails, the borrower must deposit a rebalancing amount.
Stress Scenarios:
| Scenario | Cost Overrun | Delay | Additional Equity | In-Balance? |
|---|---|---|---|---|
| Base | 0% | 0 months | $0 | Yes |
| Cost +10% | +10% hard costs | 0 months | $X | |
| Delay +3 months | 0% | +3 months | $X (interest carry) | |
| Delay +6 months | 0% | +6 months | $X (interest carry) | |
| Combined stress | +10% | +3 months | $X |
Step 6: Hedging Strategy (Floating-Rate Components)
Compare three instruments at 2-3 strike/rate levels:
| Instrument | Terms | Upfront Cost | Effective Annual Cost | Protection Level |
|---|---|---|---|---|
| Interest rate cap (strike 1) | SOFR cap at X% | $X | $X/year amortized | Protects above strike |
| Interest rate cap (strike 2) | SOFR cap at X% | $X | $X/year amortized | |
| Interest rate swap | Fix at X% | $0 upfront, breakage risk | $X net (fixed - received float) | Full protection + exposure |
| Collar | Cap at X%, floor at X% | $X (can be zero-cost) | $X/year | Bounded protection |
Breakeven rate analysis: At what SOFR level does property DSCR hit 1.0x? The cap strike must be at or below this level to provide meaningful protection.
Lender compliance check: Does the proposed hedge meet lender requirements for strike, notional, term, and counterparty rating?
Decision framework:
- Cap for bridge/transitional: no breakage risk if early exit; worst case is losing the premium
- Swap for long hold/permanent: rate certainty; but breakage costs can be six figures if early exit
- Collar for cost optimization: cap + floor; zero-cost if floor income offsets cap premium
Step 7: Recommended Structure
Narrative (5-8 sentences) covering:
- Which structure is optimal and why
- The tradeoff between return maximization (more leverage) and downside protection (less leverage)
- Conditions under which the recommendation changes (rate movement, NOI performance, market)
- Hedging approach for any floating-rate components
- Construction-specific risks (if applicable): cost overrun, delay, lease-up
Output Format
Present results in this order:
- Capital Structure Alternatives -- 3-5 complete structures with all terms
- Comparative Metrics -- side-by-side return and risk metrics
- WACC Decomposition -- tranche-by-tranche cost with marginal cost inflection
- Leverage Sensitivity -- value change impact on equity by structure
- Construction/Bridge Section -- budget, draws, interest reserve, in-balance, stress (if applicable)
- Hedging Strategy -- instrument comparison with breakeven and compliance (if floating rate)
- Recommended Structure -- narrative with rationale and conditions
Red Flags & Failure Modes
- Ignoring the marginal cost inflection: Adding mezz at 12-14% to an asset returning 8% unlevered is value-destructive. The WACC decomposition must identify this break point.
- Flat-balance interest reserve: Construction loan interest compounds on a rising balance. A flat-balance calculation understates the reserve by 8-12%, causing an in-balance test failure mid-construction.
- Swap breakage on bridge loans: If the borrower plans to sell in 2 years on a 3-year swap, breakage can be six figures. Caps have no breakage risk.
- Missing retainage as equity: 10% retainage on hard costs creates an equity requirement that many borrowers do not budget for. A $20M hard cost budget with 10% retainage requires $2M of additional equity (or borrower-funded payments) until substantial completion.
- Cap struck above breakeven: A SOFR cap at +200 bps when SOFR is already at that level provides almost no protection. The cap strike must be at or below the DSCR 1.0x breakeven rate.
- Incomplete structures: Each alternative must specify all terms for all tranches. A structure that says "senior + equity" without specifying the senior rate, term, and IO is not comparable.
Chain Notes
- Upstream: loan-sizing-engine (senior sizing), mezz-pref-structurer (subordinate terms), JV waterfall (equity structuring)
- Downstream: deal-underwriting-assistant (optimal structure feeds return calculation), refi-decision-analyzer (capital stack reconfiguration at maturity)
- Peer: sensitivity-stress-test (leverage sensitivity methodology shared)