
Explanation:

Box 1: Yes
Once you have defined a skillset, you must map the output fields of any skill that directly contributes values to a given field in your search index.
Box 2: Yes
The definition is a custom skill that calls a web API as part of the enrichment process.
Box 3: No
For each organization identified by entity recognition, this skill calls a web API to find the description of that organization.
Reference:
https://docs.microsoft.com/en-us/azure/search/cognitive-search-output-field-mapping