For a Jekyll trial, move a small set of real pages with images, navigation, and front matter. Run the build locally and in the intended hosting pipeline, then check links, generated URLs, search behavior, and the editing process for nondevelopers.
Static output is simple to serve, but plugins and build tooling still need maintenance. Time a content update from draft to publish, and keep source files in version control. Choose Jekyll when the authoring and deployment workflow is as comfortable as the final site.
Akousa