Have plently of experience with this. I met my exabf abt 4 yrs ago, and did an official coun't on his cell phone losses about 2 years into the relationship. I figured out (of all that I can remember) he "lost/broke/had stolen" (SOLD is more like it...) at LEAST 39 phones... in two years! And yea, he'd replace it with the insurance, once that ran out, he'd just add a new phone line onto his plan, and suspend the old one... or just outright buy a new phone, or have his family buy a new one. Either way, lots of phones "lost". Oh, and he did admit to it... everytime, after about a week or two of asking lol. Then he'd lie about it the next time, all over again.
There were even times he'd get enough money, get his phone replaced, and a few hours later another one was sold. And yep, I've bought them back from the dealers themselves (ex said he sold it for $15, I'd end up paying $50... grrr). If only I could've known then what I know now.