Elliott's 2026 Investment Playbook
Elliott Caldwell’s 2026 Investment Playbook
Resort-Style Short-Term Rentals Built for Control, Cash Flow, and Long-Term Relevance
A Clear Framework for the Next Phase of Short-Term Rentals
The short-term rental industry has matured. Generic Airbnbs, copy-paste properties, and thin margins are becoming increasingly fragile as competition and regulation rise.
This page is a brief overview of the investment framework outlined in Elliott Caldwell’s 2026 Investment Playbook—a control-first strategy focused on large, resort-style short-term rental assets designed to outperform across market cycles.
The full document goes deeper. This page answers one question:
Why this strategy—and why now?
The Core Idea: Control Beats Prediction
Rather than relying on appreciation, timing, or hype-driven markets, this playbook centers on intentional asset creation.
Each property is designed to:
- Control the guest experience
- Control revenue drivers
- Control operating margins
- Control tax outcomes
- Maintain long-term relevance
At an average investment size of ~$1,000,000 per property, these assets sit in a strategic middle ground—large enough to create meaningful impact, small enough to remain agile.
Why Resort-Style Short-Term Rentals?
Large, resort-style short-term rentals operate in a different category than entry-level Airbnbs.
They are:
- Destinations, not commodities
- Experience-driven, not price-driven
- Built for groups, families, and events
- Designed to compete with hotels and boutique resorts
This shift dramatically changes the economics by reducing competition and increasing pricing power.
Who This Is For
This strategy is designed for:
- High earners seeking tax-efficient cash-flowing assets
- Investors who value durability over hype
- Operators focused on long-term ownership, not short-term speculation
- Anyone who believes real estate should be engineered, not guessed
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