Hopefully my data point will still be relevant as it relates to a purchase protection claim filed in early 2016 (just saw this thread otherwise I would have contributed earlier). I had purchased a Nexus 5X phone for my sister in late Dec 2015 and in early March she left the phone on the bus on her way home from school. I reached out to the bus company via email to see if they could look for the phone but it was never located. I opened a case with thru the Chase Benefit portal and described where and at what time the phone had been left behind. Chase requested something in writing from the bus company stating that they had searched but could not locate the phone. After some back and forth I was able to get someone from the bus agency to reply back that they had search and had no luck locating the phone so I printed the email exchange to PDF and submitted it as proof. My claim was processed within a few days of submitting the email exchange and I was refunded the full cost of the phone.
Items submitted: Original Receipt for Phone, Chase Sapphire Preferred billing statement with the purchase highlighted, lost and found initial report made to bus company, and reply from bus company stating they tried looking but did not locate phone
All of my interaction was completed thru the online benefits portal and it was approved with little pushback within 20 days. I believe the process would have been shorter had it not taken so long to get a reply back from the bus company.