Which design (using OOP) is better? Ensure reporting/logging of an object is externalized or internalized?

I am building this tool for comparison of properties in two resources that can be of type - JSON, properties, VMs, REST API, etc in Python.

The tool reads a metadata json having a structure like follows:

{
  "run-name": "Run Tests"
  "tests": [
    {
      "name": "Test 1",
      "checks":[
         {
          "name": "Dynamic Multiple",
          "type": "COMPARE",
          "dynamic": [
            {
              "file": "source.json",
              "type": "JSON",
              "property": "topology.wlsClusters.[].clusterName"
            }
          ],
          "source": {
            "file": "source.json",
            "type": "JSON",
            "property": "topology.wlsClusters.[clusterName == ${1}].Xms"
          },
          "target": {
            "file": "target.properties",
            "type": "PROPERTY",
            "property": "fusion.FADomain.${1}.default.minmaxmemory.main",
            "format": "-Xms{}?"
          }
        },
      ]
    }
  ]
}