Apple
I've been using Apple devices since 2001, but I'm curious about exploring Windows for its Windows Subsystem for Linux (WSL) and how Satya Nadella is now leading the direction of Microsoft.
I enjoy the Apple ecosystem for its integration. I won't say I'm an Apple enthusiast, but I really enjoy the integration across devices.
Pros:
  • Integration across devices
    • Easy to switch devices which your AirPods are connected to
    • Copy/pasting works seamlessly across devices
      • Handover is nice
      • Airdrop is convenient
  • Devices retains value
  • Thieves nowadays are less inclined to steal Apple devices as they hard more difficult to unlock
  • Apple Health integration
  • Tracking of devices
  • Family support
    • Family sharing
      • Purchase Sharing
      • iCloud Storage
      • I don't use:
        • Apple Music
        • Location Sharing
        • Screen Time
  • Seamless migration between devices
    • For example:
      • iPhone 6S to iPhone X
      • iPad Pro 2017" to iPad Pro 2018"
    • Support by iCloud
Cons:
  • Apple ecosystem has gotten expensive
    • Devices
      • MacBook Pro 15": $1,999
      • Apple Watch Series 4: $399
      • iPhone X 256GB: $1149
      • iPad 2018 256GB: $949
      • AirPods: $159
      • Total: $4,655
    • Subscriptions
      • Apple Family: $2.99/month for 200GB
        • I personally think this is reasonable
Wants:
  • Cheaper devices
  • AirPower
  • Apple Health app for iPad, and macOS
    • I want to be able to view my Apple Health information on my different devices
  • MacBook Air 15"

  • Check MacRumor's Buyer's Guide on when to best buy one
  • Ideally soon after launch
    • Apple doesn't releases devices often, so this is the best way to maximize the value of the latest device

  • Buy refurbished:
  • BHPhotoVideo offers discounts once in a while
    • No taxes if shipping to states outside of California
  • After the launch of a new device
  • Wait till sales periods
    • Black Friday and Cyber Monday, late Nov
    • Christmas sales

  • Spring refresh in late march

  • WWDC
    • Announcement of new macOS
    • Announcement of new iOS

  • New MacBooks

  • Announcement of new iPhones

  • New iPhone launches
  • new iOS launch
  • new macOS launch

  • Announcement of new iPad Pros

  • New iPad Pros
  • Black Friday and Cyber Monday sales

  • Christmas sales
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Buying a Device
Options to buying cheaper:
Yearly Schedule
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