Any reason NOT to do AP bridging like this?

Solo trip coming up in November with 5-day park hoppers, staying at Pop using the fall/holiday package discount. Family trip scheduled in April with 8-day park hoppers (current reservation is POFQ but this is subject to change - also considering CBR depending on how the Skyliner goes or possibly a deluxe if a good promotion comes out). Planning to upgrade to AP on my arrival day in November, applying my ticket price to the AP price. I’ve run the math on the tickets and the AP will cost me $95 more than just the tickets, but I will save when you factor in Memory Maker and other AP discounts. There is also probably a 75-80% chance I will be back at least one more time before the AP would expire.

I am wondering how this will affect our Spring 2020 trip though. Can someone help me understand how I would book a package (including dining plan and tickets for my husband & daughter)? I think I read that you can only add the dining plan to a room if it’s been booked with the AP discount. Also, how does this affect things if there is a promotional package discount or room discount?

You can always book a room and dining package. It is called a “ticketless package”. You need to call to book it. You could apply room discounts to that package but you could not book any discounted packages that require tickets.

You can buy tickets from Disney or a discounted seller. Use the touring plans ticket calculator!