In today's episode, we're diving into how Skylight Calendar's innovative AI tool, Sidekick, is transforming the way busy families manage their schedules. Reporter Jennifer Pattison Tuohy recounts how, during the hectic spring sports season, forwarding emails and snapshots of schedules to Sidekick has become a “godsend” that smartly parses the data and updates multiple calendars at once. With a sleek 27-inch display—the Skylight Calendar Max—this device not only organizes family events across platforms like Google Calendar but also doubles as a digital photo frame and even offers AI-driven meal planning. While its convenience and clear display are major wins, there are also some caveats: an annual subscription fee that has recently doubled to $79, limited two-way sync (only with Google), and some underwhelming aspects of its meal-planning feature that still have room for improvement.

Key Points:

• AI-Powered Organization: Sidekick can transform emails, photos, flyers, and spreadsheets into calendar events, streamlining the organization of multiple sports practices, games, and family events.
• Impressive Display: The Skylight Calendar Max boasts a large 27-inch touchscreen with 2560 x 1440 resolution and an anti-glare screen that makes it easy for the whole family to view their schedules.
• Subscription Costs & Features: The enhanced organization comes with a “Plus” subscription costing $79 per year (recently raised from $39), which also includes digital photo frame capabilities and an AI meal-planning feature.
• Calendar Sync Limitations: Two-way calendar syncing is supported only with Google, so families using other calendar services may face some challenges.
• Additional Functions: Besides scheduling, the device offers tabs for meal planning, chore charts, and to-do lists, though the meal-planning function needs more customization options.
• Privacy & Usage: Skylight adheres to strict data privacy practices by encrypting all data and allowing users to delete it easily, ensuring your family’s information stays secure.
• Competitive Landscape: Compared to alternatives like the Echo Show 21 and Hearth display, Skylight focuses on being a dedicated calendar assistant with powerful AI import capabilities.

Stay tuned as we explore the intersection of smart home technology and family organization—this could be the game-changing tool you’ve been searching for!
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