DVC (and our dues $) would have to invest in quality computer engineers to initially create the program AND keep some of these people on to maintain it. My brother is a computer engineer just out of college and said it would not be difficult to create this system. Caskbill's wonderful DVC-Planner would be a great template for the program.
The system that DVC would require is in no way comparable to Caskbill's planner (wonderful though it is). That's like comparing Marriott's reservation system to Caskbill's planner. But this would be even more complex than your typical online hotel reservation system, because of multiple contracts, cancellation windows, banking windows, rooms booked for cash, linked reservations...ugh. Gives me a headache just thinking about it.
Technical feasibility isn't the problem here; while complex, it's certainly not impossible. FINANCIAL feasibility is the issue. A system of this nature would require a good-sized team of design analysts, engineers, database analysts, testers, etc. Those people don't just leave when the site goes live...there are bug fixes and enhancements to do. Then, you have to host the thing on servers than can handle the load when thousands of members decide to book the first week of December...all at the same time. Add in some people to manage the servers. Add in the cost of maintenance upgrades to the server's OS, and assorted 3rd party software.
In short....a system like this is very expensive to create and maintain.
Very expensive. Where, exactly, does DVC recoup the cost? Yes, they can lay off some of their MS staff, but certainly not all of them. MS does more than just take reservations. I'm sure DVC has done the cost analysis for this backwards and forwards. If there comes a time where they think they can get their development and maintenance costs back, they'll do it. If not, they won't. Simple as that.