Having dealt with MANY phones and services in the past, I can say with 99% certainty, customer service starts with how you explain the problem. Tone of voice, clarity of the issue, desired result or options of results that will satisfy you all come into play. Almost ALL customer service reps CAN push through just about any upgrade or swap regardless of how long you've had the phone, depending on what the problem is.
I went through 2 Droid Bionics, 2 Droid Razr's, and a Galaxy Nexus (or Prime as it is sometimes called). On the last swap I called in, explained my issue, and received my iPhone 4S, case, car charger, screen protector, and $25 credit on my acct. Total cost to me: $0.00 and about 30 minutes on the phone. New one was overnighted free of charge. In exchange all I had to send back was ONLY the old phone itself.
All my issues were phone hardware specific (not my doing), or software related.
Sold almost all the other accessories on eBay, still have some for the Bionic left though...
In any case, when my wife needed a new phone, I told her to get a Droid. Why, if I have an iPhone, did I do this? Simple, I know that it'll be easier for her to get the hang of it, because she can customize it to her liking. I love my iPhone, but do appreciate the "open market" of the Droids.