It's not a dumb question, because it is a complicated comparison. (I didn't have time to do it at work, earlier.)
The cost of an adult
DVC annual pass is $419 + 6.5% sales tax = $446.24.
Look at the discounts on the
Undercover Tourist site to find the ticket with the biggest discount (the orange column), but at the same time has a gate price less than $446.24.
With the MouseSavers discount, the best ticket is the 6-day Park Hopper. ($29 off the gate price.)
Here's how it works, this time with the numbers.
Buy the 6-day adult park hopper ticket from UCT using the MouseSavers discount and pay $304.95. (This price includes the tax and the shipping.)
Use the ticket at WDW at least once, and then upgrade it to a DVC Annual Pass.
WDW will give you a credit of $334.41 for this ticket toward your upgrade. ($314.00 + 6.5% sales tax)
You should pay $111.83 for the upgrade. ($446.24 - $334.41)
So in the end, you've paid a grand total of $416.78 for your DVC annual pass, and saved $29.46.