Even though I get it and love it for what it is, part of me would still love The Trip (even more) if it could take a once a month trip onto WDW resort properties like the Poly or WL to report on seasonal activities, new restaurant menus, new bar experiences (eg Trader Sams), etc. Maybe ride the on property transportation like the monorail, the bus and the boat to get from one spot to another and address transfers and where you have to go and what you have to take if eg you just had dinner at Sanaa but now want to get to the beach at the Poly to watch the fireworks. Possibly look at a non-park day and what to do including Disney Springs, resort hopping, etc. There also seem to be quite a few DVC owners/renters on the boards and while I'm not one and don't have much interest in becoming one, there is likely an audience out there hungry for more info about renting DVC points, which properties to stay at, what restaurants on DVC properties are worth going to, etc.
Its a hard balance. The Trip has to be new and different. But selling new and different to WDW lovers who really love to hear about WDW isn't always easy.