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It is possible to create several checklist items and groups (headers) at once - simply paste multi-line text into item creation field and then press Enter.

Multiline paste and creating several items at once is useful for:

copy-paste bullet point list of items from external list (issue Comment or Description, Trello, web page, MS Word, etc.),
compiling a checklist in a favorite text editor before entering it into Jira.
paste checklist copied from another issue

Paste multi-line text (e.g., bullet list copied from the web page or Word):

Issue Checklist Documentation (Legacy) > Paste multiline text (create several items at once) > paste-multiple-items-before.png

and get the following checklist:

Issue Checklist Documentation (Legacy) > Paste multiline text (create several items at once) > paste-multiple-items-after.png