A strategic guide for high-income Florida investors evaluating Orlando short-term rentals across acquisition, operating years, and exit. It focuses on sequencing, NIIT, ownership structure, and long-term tax tradeoffs.

A portfolio-level framework for high-income Florida investors to coordinate timing, activity posture, depreciation strategy, and exit readiness across multiple years.

Florida landlords don’t have a state income tax to manage, so federal sequencing becomes the main lever. This guide frames exits around income stacking, NIIT, depreciation unwind, and structure-driven flexibility.

A portfolio-level decision framework for Florida investors weighing hold, exchange, or sell choices. Built around sequencing, optionality, and exit-aware planning.

Federal tax rule changes taking effect in January 2026 will reshape how Florida real estate performs after tax. This guide explains what high-income investors need to know about timing, structure, and long-term outcomes.

Short-term and long-term rentals are not just different operationally. They produce very different tax outcomes once depreciation timing, active versus passive treatment, entity structure, and exit planning are considered. This guide breaks down what matters over a 10-year horizon for high-income Florida investors.

Depreciation recapture in Florida can surprise even seasoned real estate investors. Learn what it means, how it’s calculated, and how to reduce or defer it through smart tax planning and 1031 exchanges. Square Accounting explains the rules and helps you keep more of your profit.