I've done the Premier Passport twice now and just cashed in on the DVC renewal (first time ever for DVC to offer a discount on the Premier Passport. I think it was $849 - a total no-brainer for someone who goes to the parks 3 or more times in a year!
As some others have said, not only are the food discounts well worth it (CM's are actually REALLY good at asking if you have an AP for a discount at food and merch locations!), but the merchandise discounts are phenomenal as well! 20% discount and that has included everything that we've encountered in Downtown Disney as well (Lego store!!).
The $99 is similar to what you would pay for Tables in Wonderland, except you get the food and merch discounts.
Something to consider in the future: if you end up getting the Premier Passport, it gets you into the waterparks, Wide World of Sports, and I think the miniature golf, etc. at WDW. In the past, when I had only a WDW AP, I didn't purchase the premium AP because I didn't have a strong desire to go to the waterparks. However, last year, with the Premier Passport including entry to waterparks, I visited Typhoon Lagoon for the first time in more than 15 years or so. It was nice because I didn't feel like I had to stay all day "to get my money's worth" since it was a part of my pass that I never actually planned to use.
All in all, I have been
very happy with the Premier Passport (besides the back and forth intricacies going between WDW and DLR). It has given me some great opportunities to visit "when I have been in the neighborhood" when I otherwise would not have had the chance!
Also, as an FYI, I purchased my previous one as well as my recent renewal vouchers directly from the ticket windows in the promenade between Disneyland and California Adventure without any problem.
Be forewarned: Premier Passports issued by DLR are NOT RFID-enabled, so they will not work at WDW. If you return to WDW before it expires, they will have to swap out the pass for one that is RFID-enabled. Also, if you go to DLR with the RFID-enabled Premier Passport issued at WDW, it will NOT work at DLR. They will take the pass info and do a back-end fix, but it takes a few days. The whole thing is a mess and time consuming. At DLR it was finally working on the last day of my trip.
FYI, I acknowledge the fact that the DLR-issued pass has not had the RFID capability, however, my current pass was issued at WDW, with RFID. The biggest frustration is that I have not been able to associate it with the MagicBand and MyMagic+ systems.
However, when going to DLR, there was no distinct problem with using the ticket other than the fact that Disneyland's picture database system which they use for AP's didn't integrate well. I could use my ticket at the gates but they would always tell me to go have my photo taken for the database. After pursuing this twice and having my photo taken and supposedly linked to my account, they continuously asked me at the turnstiles to go get my photo taken.
It wasn't until I just recently got my renewal ticket that the gracious CM mentioned "hmm, your ticket's Photopass # isn't in the system..." She set it up on the spot and told me I could have my photo taken by any Photopass photographer. I did the same morning and it was in the system the same day without any more questions from the CM's at the turnstiles!
After having the Premier Passport as long as I have, it's hard to turn back to anything else with the per-visit ticket prices for Park Hoppers.
And now, when ridiculously cheap flights come along...or I have a business trip that passes
very close to DLR, I can always excuse a stop by the Happiest Place on Earth!
Enjoy your trip!