Welcome to the Disney Parks Moms Panel, Amanda!
I am a huge fan of
Memory Maker. It is a great value, and even more so if you can make it work to include two trips. You have asked a tricky question. However, I
think you might be able to make this work!
Here is the tricky part. Your Disney's PhotoPass photos expire 45 days from the date taken, so you must activate your Memory Maker entitlement during that window. Memory Maker is valid for 30 days AND will allow you to download any additional photos taken during those 30 days. Depending on your trip dates, you may be able to activate Memory Maker so that it will cover both trips.
I was able to do this last fall with a planned trip and an unexpected one. My family visited the resort during Halloween with our first photo being taken on October 29. A few weeks after our trip (November 22), I activated my Memory Maker entitlement. I soon learned that I was chosen for this panel and would be heading back to Orlando for training mid-December. The last photo from training was taken on December 15. Since Memory Maker was valid for 30 days from the date of activation, all the photos I collected during my training trip were available for me to download. It was a magical win-win!
I hope this helps, and I am sending loads of pixie dust so your Memory Maker entitlement will cover both of your upcoming trips!
Missy