I've actually been very pleased with the update support from Verizon/HTC for my aging Droid Incredible (original, not version 2). This phone started out with 2.1 (Eclair), and shortly received an update to 2.2 (Froyo). The phone was actually 'end-of-life'd this past March but that didn't stop them from providing an update to 2.3 (Gingerbread - the latest version available for phones prior to 4.0's imminent release) just this past September. These are all vendor-sponsored updates mind you, no CyanogenMod required.
So essentially, I've been provided with an update to the latest Android every time a new version has come out since the release of the phone. Can't ask for much more than that.
That's not to say that I'm necessarily expecting an update to 4.0 (Ice Cream Sandwich), but with today's uber-short product lifecycles I'm pretty happy with the support for this 1.5-year-old phone. And if they *do* update the Droid Incredible to 4.0, that's going to significantly enhance my loyalty to Verizon/HTC to the point where I'll probably insist on the same carrier/vendor when I upgrade.