Checklist with a unique scenario

[rbalamu2]

Hi Team, 
I have this below scenario

I need a field which is of a select list with 3 options like below
Field Name : Test Field
Option 1     :  ✅ Yes
Option 2     :  🟥 No
Option 3     : ⬛️ N/A


Clicking on option 2 or option 3 should populate a text box where user can enter their comments. 

Also, I want the checklist/option color to be shown in the report or jql when we try to see it. ( but this is secondary)

I could see some plugins in marketplace which has the option to do the checklist for issues but I need a plugin or an alternative which can satisfy this scenario.