Backlog Item Categorization by Value and Risk

I'm a Product Owner managing a backlog of 47 items. 
Categorize these items into four buckets: 
1. High Value, Low Risk (ship first)
2. High Value, High Risk (prioritize but plan carefully)
3. Low Value, Low Risk (do after high-value items)
4. Low Value, High Risk (consider dropping)

For each bucket, list the items and explain the categorization logic.

Backlog items:
[paste your list]