Four sets of rules come up on a Naples roof job: the local water rule, the insurance statute, the association's covenants, and the state's contractor licensing law. Each is quoted here so you can check it yourself.
Water use: allowed any day under the county rule, with the right equipment
Collier County's Ordinance 2015-27 sets the standing Phase I water restrictions for the county, and the county's own summary of it reads: “Other outdoor water uses, including car, truck, and boat washing, and the washing of exterior home surfaces and roofs, shall be allowed anytime with the use of Low Volume Pressure Cleaning Equipment, Low Volume Mobile Washing Equipment and/or water hose equipped with an automatic self-canceling or automatic shutoff nozzle. In all cases, the water used must drain to a pervious surface or to a water recycling/reuse system.” A roof wash is not tied to the odd-and-even irrigation days. For a paver driveway, the paver cleaning and sealing page takes it from there. The county's summary does not say how far the rule reaches inside a city, and it is not the rule for an Estero or Bonita Springs address, so for a given address the city or the water utility can say which rule is in force.
During a declared water shortage a second rulebook applies. The South Florida Water Management District's Chapter 40E-21 restricts “outside pressure cleaning” to “only low volume pressure cleaning” in the text for every phase, seven days a week in Phases I and II and on fewer days in Phases III and IV. Those restrictions apply only after the district declares a phase, and the district's order declaring a phase can modify them, so the days in force are the order's. The district posts the current status on its landscape irrigation page.
Insurance: the 15-year rule
For an insurance question, the statute is the place to look, not a cleaner. Florida Statutes 627.7011(5) says an insurer “may not refuse to issue or refuse to renew a homeowner's policy insuring a residential structure with a roof that is less than 15 years old solely because of the age of the roof,” and that for a roof at least 15 years old the insurer “must allow a homeowner to have a roof inspection performed by an authorized inspector at the homeowner's expense before requiring the replacement of the roof of a residential structure as a condition of issuing or renewing a homeowner's insurance policy.” If that inspection shows “5 years or more of useful life remaining,” age alone cannot be the reason for a refusal. A cleaning changes how a roof looks. It does not change its age, and under the statute the useful life remaining is what an authorized inspector's inspection indicates. Whether a clean roof satisfies a particular carrier's letter is a question for that carrier.
Your association
Florida Statutes 720.3035(1)(a) limits an association's authority over “the external appearance of any structure” to what is “specifically stated or reasonably inferred” in “the declaration of covenants or other published guidelines and standards authorized by the declaration of covenants,” and requires that those standards be applied “reasonably and equitably” to all parcel owners. Florida law does not itself require anyone to clean a roof; the covenant does, if it does. In a condominium, Florida Statutes 718.113(1) reads: “Maintenance of the common elements is the responsibility of the association, except for any maintenance responsibility for limited common elements assigned to the unit owner by the declaration.” Whether a roof is a common element, and who orders its cleaning, is the declaration's to say.
Licensing: what Florida does and does not license
Florida's contractor licensing statute, Chapter 489, has no category for roof cleaning, pressure washing or window cleaning. The seventeen categories in section 489.105(3) run from general contractor through roofing contractor to the pool, plumbing and solar trades. Section 489.117(4)(a) goes further and names “pressure washing” among the job scopes for which a local government “may not require a person to obtain a license,” while a local government may continue to offer a license for several listed scopes, among them “rooftop painting, coating, and cleaning above three stories in height,” “if the local government imposed such a licensing requirement before January 1, 2021.” The Collier County Tax Collector states that any business operating anywhere in the county, inside the Naples city limits included, must have a county business tax receipt, and that there are a few exceptions. The licensing line that matters on a roof is the coating clause quoted above: under 489.105(3)(e), coating represented “to protect, repair, waterproof, stop leaks, or extend the life of the roof” is within a roofing contractor's scope.