Rub your hand across a sun-facing wall. If it comes away with colored powder, the paint is chalking and has lost its protective binder; that is the clearest sign a South Florida exterior is due for repainting.
Other signs: visible fading on west-facing walls, hairline cracks in stucco, peeling at the fascia and window trim, and black or green mildew on shaded sides of the house. Cracks matter most, because summer rain gets into them and damages the stucco behind the paint.
Most well-prepared exteriors last seven to ten years here, and interiors five to ten depending on traffic. Coastal homes, dark colors and walls with full afternoon sun are at the short end of that range.
The dry season, roughly November through April, is the easiest time to schedule an exterior: lower humidity, fewer afternoon storms and more predictable drying. Exterior work is still possible in summer with morning starts and a flexible schedule; interior painting works year-round.
If you are not sure, a Nova Spaces walkthrough will tell you what needs attention now and what can wait, in a written proposal with a fixed price.