We did from 2017-2018.
We go every year for Christmas from 12/24-1/1.
After our 2016 Christmas, my cousin said she wanted to bring her little ones and insisted on us coming. She planned on going from 10/28 - 11/5. After playing with the numbers, we decided to become AP holders right before the
ticket prices went up.
We then found really cheap airline tickets for Easter. Having never been, we decided to go.
So now we had gone the following dates:
4/15/17 - 4/18/17: First Easter
10/27/17 - 11/1/17: Halloween family vacation
12/25/17 - 1/1/18: Christmas
1/27/18 - 1/29/18: Quick trip for Pro Bowl practice - did go to the parks once
3/29/17 - 4/2/17: With Easter falling earlier this year, we were able to sneak in one more trip
Not gonna even count the park tickets, because it was a wash. We easily exceeded the breakeven point.
Where you spend the money is the resorts, the souvenirs, the food, travel, etc.
We are Southwest Rapid Reward Members. Everything goes on my Chase Sapphire Reserve or on our Southwest Card. This allows us to use points to travel here and there. We rarely have to purchase a flight. If used correctly, your cards can work for you.
PhotoPass: just based on our trips, we saved $750. That's almost enough to cover one AP.
Food: We didn't purchase the TIW card since we'd be traveling during peak dates, when the card isn't accepted at most restaurants. Instead, we either went on the
DDP (just easier for us) or paid OOP and used the AP discount. We happened to go while the AP discount was 20% in most locations and that really saved us a lot of money.
Resorts: Sometimes you get a really good deal. During our first easter trip, we paid (on average) $180/night at Coronado. There's no discounts during Christmas. We went through a TA during Easter 2017 and stayed at YC. We scored a decent rate at Poly for Halloween, but it was def expensive.
All in all, if you're gonna go a decent amount and
time your trips right, then the AP could be a really solid value. You're not gonna beat the system. A Disney trip is a Disney trip and is expensive any way you cut it, but having the AP helps cut unnecessary costs and locks you into a flat rate for that year—so if Photopass goes up in June or ticket prices go up (as they have), you've already paid $850. This is kinda what happened to us when we purchased it. Ticket prices went up the next day and made it an even bigger value.
What i will say, is that I'm not sure this year is a good value. The parks are gonna be PACKED - not just with your normal Disney fans, but SW fans who are going for the first time. Now... maybe this makes it
more worth it for you, but for us...we're taking some time off.