There is a loophole in Disney's ticket policy that you can take advantage of if you want to save a little extra on annual passes. Specifically, the policy has to do with the value Disney assigns to your current ticket when doing an upgrade.
If the ticket has never been used, Disney will give you credit for the actual amount at which that specific ticket was purchased from them. However, if the ticket has been used, Disney will give you credit for the amount they're selling the same ticket for at the gates that day (aka the gate price). So, the trick then is to get a higher credit for your Magic Your Way tickets than you paid for them by exploiting this policy and upgrading
used discount tickets.
About the best discounted price you'll find for MYW tickets is through
Undercover Tourist. But to get their best price, you need to use a link that comes in a monthly newsletter from
MouseSavers.
The trick is to find the ticket with the best discount that has a gate price that's less than the value of the
DVC annual pass to which you want to upgrade. (This last part is important because Disney won't refund you the difference if the annual pass to which you're upgrading costs less than the MYW tickets you're trading in.)
So, to summarize the process, you need to purchase MYW tickets from
Undercover Tourist (or another discount ticket broker), use them at least once to enter a park, and then take them to a Guest Relations location to upgrade them to DVC annual passes.
You can upgrade a MYW ticket for 14 days after it's first use so long as there's at least one day left on it. However, because you get perks for being an AP holder (10% or 20% merchandise discounts at all locations being a biggie), you'll probably want to upgrade immediately. We usually go through the gate with our MYW tickets on our first morning, and then head immediately into the in-park guest services location to do the upgrade.