Hi Balaji,
Could you edit the column in Quick Edit? If yes, what CU did you install for your SharePoint 2013?
Based on my testing, if I created multiple checkboxes with Fill-in option, I could not edit the column in Quick Edit mode.
In Quick Edit mode, to edit choice column, I need to use one of the following options:
- Checkboxes (allow multiple selections) without Allow 'Fill-in' choices
- Drop-Down Menu with Allow 'Fill-in' choices
A similar post for your reference:
https://sharepoint.stackexchange.com/questions/202699/sharepoint-2013-not-able-to-bulk-edit-checkbox-columns-in-custom-list
For issue 3, after you changed the column or the file, to make sure the change is searchable, you need to run a crawl. So, please do a full crawl for your content source. After finishing, have a try again, compare the result.
Thanks,
Wendy
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