Walk any street in Sarasota or Bradenton and you'll see the pattern: homes painted three years ago that already look chalky and faded next to ones painted eight years ago that still look sharp. The difference is almost never the color. It's the prep and the product.
Stucco chalks. UV breaks the surface of old paint down into a fine powder, and new paint applied over that powder is bonding to dust, not the wall. Pressure washing removes it, and on badly chalked walls a bonding primer is the only thing that gives the finish coat something real to grab.
Hairline cracks and rotten wood have to be dealt with before paint, not after. Elastomeric patch on stucco cracks, replacement boards for soft fascia and trim, and primer on every bare spot. Paint over rot just hides it until the next rainy season.
Finally, the product matters. A 100% acrylic exterior paint with real UV resistance costs more per gallon and lasts years longer. On a whole-house job the paint is a small share of the total, so cheaping out there is the worst trade you can make. Ask your painter what they're using and why.