Comparison

Trailhead and iOverlander are not trying to be the same thing.

iOverlander is useful for finding spots. Trailhead is being built around route planning, offline packs, map layers, and field handoff.

iOverlander is useful because people have added a lot of places. That does not automatically make it a route planner, an offline map system, or a trail-building tool.

Trailhead is more opinionated. Camps, reports, pins, trails, route geometry, GPX, credits, and offline packs should live in one planning flow.

The goal is not to insult another app. The goal is to avoid pretending a long list of pins is the same as a field-ready route.