Your understanding of retailing logic is right, but VM may or may not drop a new product for the holidays. If they do, it could be on a feature phone rather than a smartphone. (I'm just guessing - I haven't seen anything that suggests they plan to do this.)
VM and the other pre-paid carriers aren't in the newest/best/awesomest handset arms race by design. The post-paid carriers have to have lots of handset choices and offer the latest and greatest because it's an incentive to pay 2 to 3 times as much as we do for functionally similar service. If you could get the iPhone 5 or the HTC Super Awesome (or whatever) from VM and pay $35 a month, I'm sure many, many Sprint post-paid customers would defect costing Sprint hundreds of millions in revenue. As long as VM's prices are so much cheaper than Sprint's, I would not expect VM's handset offerings to get too fancy.
Good point. I wouldn't call the OB fancy. If the triumph keeps costing them money in returns maybe they'd put out the OB as a consolation.