With Android updates happening at least twice a year, it's important to know where you stand in regards to getting them. According to an article over at Computerworld, going with HTC and Verizon had your upgrade to Android 2.2 (Froyo) come faster on average than any other coupling of carrier and hardware. This will most likely reign true again with the Android 2.3 (Gingerbread) update as well.
The only way to truly stay current would be to go with a Nexus phone, which (fingers crossed) could be coming to Verizon with 4G in February. To see where your phone and carrier rank, check out the chart below (click to enlarge):