The housing
Two distinct Highlands: the older streets around Base Line and Palm with houses from the 1950s and 60s, mostly composition shingle and some low-slope additions, and the East Highlands Ranch tracts from the 1980s and 90s with concrete tile on two-story stucco houses. Scattered through the north are older ranch properties with metal and shake.
The tile tracts are reaching the age where underlayment fails, and re-lays are the common job there now.
Wind
The canyon mouths above Highland funnel the Santa Anas straight down onto the neighborhoods below. Ridge caps on tile, ridge and rake shingles, and anything on a north-facing slope near the top take the brunt. After a windy night I get more calls from Highland than from any other town.
Mechanical ridge systems and high-wind nailing are standard in my Highland specs.
Fire
Much of Highland's northern edge is in a designated very high fire hazard zone, and the Old Fire burned through here. That means Class A roof assemblies, ember-resistant vents, and no debris in the valleys or gutters in fire season. A tile or metal roof with clean gutters is part of the house's defense.
Insurers here ask about the roof; having it inspected and documented helps.
Heat and sun
The east end of the valley is a little cooler than downtown San Bernardino but still hot enough to bake underlayment and shingles. South and west slopes age fastest. Attic ventilation on the two-story tract houses is often marginal, and improving it during a re-lay pays for itself.
Cool-roof tile and shingle products suit this town well.
What I do in Highland
Tile re-lays and ridge resets in East Highlands, shingle repairs and replacements on the older streets, wind damage tarping and repair every fall, and fire-season roof clearing for people on the foothill edge. Inspections for the many houses changing hands in the tracts.
Highland is a few minutes from home base, so response is fast.
What to check yourself
In fire season, look at the valleys and gutters from an upstairs window or with binoculars; any visible pile of needles or leaves needs to come off. After a wind event, walk the yard for tile fragments and ridge mortar, and look along the ridge line for caps sitting crooked. Either one is a reason to call before the rain.