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How to set column format and values on binding data

I am trying to create a grid which hopefully can look similar to a web grid i am trying to create. The Data i have comes from a RestApi in form of Json and i deserialize the data fine. When i bind it to grid it does not look the way i want it because a few issues.

a) i have a array of objects which consist of a DocId and Text. What i would like to do is display a list of all possible options as well as check all options which where selected for this record. Similar to this

b) i have a field which has a holds a array of String,string like [{"home" : "},  {"work" : "}]
how can i display this in the field like (home) ?