Extend & Conditional label conversation

Our clients request following features from us, so would like to ask if this is possible to implement:

1) Extend the conversation information with the session_id / conversation_id / user_id information

2) Conditional labeling of conversation: Clients would like to differentiate between specific conversations and label them visually (Same way as the negative/positive feedback buttons label the convesation), but automatically if specific conversations pass specific conditions (Eg.: when User_ID variable = smth, or another {VF_variable} = smth)