Here's my thoughts on the matter... let me appoligize now for what will probably be a long post, to get to my end result. If you want to skip to the last part for my opinion, that is fine, just detailing the steps that lead me to this conclusion. Scroll to paragraph starting with ***OK... for the quick answer.
I've been a Nextel to Sprint customer for over 10 years, never had any insurance on my Motorola Nextel phones, you could whip those things at a wall, and the worst thing that happened would be a scratch or 2. (yes, I have done that a few times)
In March of 2010 I decided I wanted a BlackBerry Curve, on Sprint, but wasn't sure how well this more delicate device would hold up in a rough environment (I drive a semi-truck for a living, a drop while entering or exiting the vehicle would be about 4-6 feet). So I bought the phone, at a Sprint store, along with an Otterbox Defender and the Sprint insurance.
Let me deviate for a moment to express the importance of a good protective case for your device. I got the phone on a Thursday, the following Monday I dropped it (unknown to me at the time) in the middle of a busy street (fell out of the holster, after I failed to fully secure it I believe). I went about my business, and started back down the road. Went to make a call and I was horrified to not be able to find my device in my truck. I realized the best thing to do was to retrace my steps, it had to be a in a pretty small area. So I headed back to my customer, thinking I was gonna need to look in the parking lot, as I approached the driveway, I noticed a small black object in the traffic lane of the road out front. Yup, you guessed it, it was my 4 day old BlackBerry, face down in the tire ruts in the road! I had stopped outside the lot before entering earlier and spoke with a gentleman for the place I was going, I needed his phone number for a call later in the day. As we were standing in the street, I must have dropped it there. Anyway, where the phone landed, and must have sat for a good 15 minutes, I find it hard to believe it wasn't hit by a vehicle, it may have been, but I couldn't find any indication of this, it was just fine, in good working order and no cosmetic damage other than some dirt that wiped away. Like I said, it was lying face down in the street, if that case wasn't on it, I'm sure I would have at least had a scratched screen, and probably the keyboard too. As far as phones and protective cases go, my advice, and I know this phrase is usually used in another context, but, "Wrap That Rascal"!
I few minor drops later and a year had passed without needing the insurance, and being a (at the time) Sprint Premier customer, I was still eligible for an upgrade, until the program ended at the end of that month. I could get a newer model BB Curve for free at Best Buy (was $49.99 @ Sprint). But, in March of 2011, the dropped calls on Sprint had turned just Horrible (yes, very much worse than it is today) and I wasn't sure if I wanted to sign a 2 year agreement just to get a new phone. While talking to a rep at Best Buy, he told me that if I got Geek Squad Black Tie Protection, I could also get (for an additional $30) the Best Buy-Buy Back program, where on a sliding scale, starting at 50% of the original cost of the phone for the first 6 months, I could sell it back to Best Buy. I told him great idea, so on a free phone they would give me back 50% of FREE! By my math, that's $0.00. He countered with NO, 50% of the off contract price of $469! OK, much better, that works out to about $235, enough to pay off my ETF with Sprint and have a few bucks to put towards a new subsidized device on a new carrier if I need to switch due to the dropped calls. Of course at the time there was no deductible on the insurance, and it was the same $10/mo. as Sprint. Perfect for my situation, sign me up! And as an added bonus, the new Curve had the same body as the old one, just different internals, so my Otterbox would slip right on!
Another 15 months went by, no need for the insurance, but I had it. By this time I was getting really sick of my beloved BlackBerry. I was hanging out with people that had Android and iPhones and I had my BlackBerry. It was like hanging out with people that had Blu-Ray players and DVD players and what I had was more like a 4 Head Stereo VCR with S-Video! Something that at one time was cool, but had since been passed by the technology express. I wanted an Android device, bad. While paying my bill on the Sprint website, I noticed they were telling me I was again eligible for an upgrade (to this day I still don't know WHY, but I wasn't about to argue with them about it). In just a few weeks from then, the HTC EVO 4G LTE was supposed to hit the stores on June 2, 2012. I had a goal to reach. Hit Best Buy on release day, got $140 (30% of 469) for my old BlackBerry with the Buy Back program (so many BB's I can't abbreviate much without making this confusing), a $50 Gift Card, that I could even use on THIS purchase, so the $199 phone (on 2 year contract) was only $9.00 out the door! Tack on another $30 bucks for a Buy Back plan on the EVO and another (about) $50 for a new Otterbox, and I was strolling out of the store with a big smile on my face and some great new gear for under a hundred bucks! NICE!
I had been telling people for a long time that the program that Best Buy had was awesome, and recommending it to everyone. But, if you've read his far, don't stop now, Keep reading.
On the morning of New Years Eve 2013 (just 19 days before I am typing this) I picked up my EVO, turned it on and all I could see was a bunch of brightly colored pixels in some random order. Nothing I could do would make this device usable. Things were happening under the screen, it still made noise when messages came in, I just couldn't read them (or unlock the phone, or worse yet, power it down, bad side of non removable battery). Off to Best Buy I went to stand in line at the counter. Of course the line was long, after all, it was just a week after Christmas. Finally got to the front of the line and was told they would send my phone in for a replacement, none in stock at the store. No charge for the refurbished replacement, but was told it would take 3-5 days to get to the store. I told him I needed a loaner, he said the policy had changed and they no longer did that. Let me shorten this part up, after talking to a couple of other people, one a manager, it was decided that the original contract I signed allowed for a loaner, so I could get one, but I needed to supply a $50 deposit on the loaner. So, they gave me a beat up old Kyocera Rise to use for my waiting time. By no means the perfect outcome, but it would get me by. Best Buy processed my order right away, I got a confirmation email that contained a tracking number for a UPS GROUND(?) package with a new EVO being sent to Best Buy store. Ground? I thought you told me expedited claim! Anyway, that all went down on a Tuesday, then Wed. was New Years Day, then there was a weekend, got the replacement EVO on Monday. The device is fine, battery and screen and shell are in like new condition, and I got my $50 back for the Kyocera loaner. So, 7 days later I am whole again, less a bit of screwing around to get there. I guess the long wait is at least partly to be blamed on my old EVO and the timing it had with deciding to fail.
***OK, enough background, the meat of my answer is this: Best Buy used to have a good program for insurance, and the added benefit of the Buy Back program... AT ONE TIME. It is my understanding that both of these programs have changed over this time. Or maybe I should more clearly put it, have been GUTTED! If the new insurance has a $150.00 deductible now, and the Buy Back has been discontinued, I will NOT be getting either one the next time I upgrade.
The new idea is this, I have an upgrade coming next month, (after 20 months) one of the phones I'm thinking about is the G2, that's why I'm reading here. When I buy my next phone, I will not take on the extra expense of insurance from anyone. Unlike my past devices, my EVO is still a pretty decent device by most standards, and it still works. I could trade it in to Best Buy under the terms of my original plan, and they will give me $140 for it. But, I will just eat the $30 I paid for this privilege up front and just keep my old EVO LTE for a spare. Or maybe just use it as an MP3 player that doesn't need to use the battery on my phone. An Android based MP3 player would cost more than that at about $250 or more, and would be running Gingerbread, my EVO is on 4.1.1, and HTC says it will still get 4.3 sometime next month. Also, if I ever wanted an extra line for a short time, I could just put it on Boost or Ting or even Sprint without a contract. That seems like a no brainer to me. So I say, save your old phone as a back up and forego the insurance. And don't forget a protective case.
One more piece of number crunch, insurance at $10/mo. over the course of a 2 year contract would set you back $240, if you never make a claim, that's just money you gave away. Now, say after 19 Months (too early for upgrade) you need to make a claim, you've paid in $190, then tack on that $150 deductible and you are looking at about $340 to get a refurbished device, or for almost that same money you could buy a new Nexus 5 with no contract. Of course the Nexus 5 is another one of my options anyway, so I might just buy that one outright and save my upgrade for sometime down the line. Even if you don't like these options, there are plenty of good recent phones out there that can be had for not much on the used market. Personally I think that current insurance plans are a great idea, if you are the one SELLING it, not so much if you are the one paying for it. Put your $10/mo. (or more if you can) in a piggy bank and save it as your own personal insurance. Unless you need to make a claim in the first few months, you'll be about as well off or better with deductibles factored in. And, in the first few months, the phone should have a warranty from the manufacturer.
My ideas may or may not work for you, but that is my strategy. Best of luck in whatever you decide.