Will this work if my iPad is on a family plan with my wife, but I purchased the bundle on Android, or will we need to purchase it through the app store?
I don't think so. Typically IAP carry over within a marketplace, but not across them. Theoretically the $25 Season Pass purchased on your iPad would work on your wife's iPad as well so long as they are using the same Apple ID for iTunes App Store. You would need to purchase the Season Pass again on Android I believe.