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"

Buying a Device

    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

Options to buying cheaper:

    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

Yearly Schedule

March:

    Spring refresh in late march

June:

    WWDC
      Announcement of new macOS
      Announcement of new iOS

July:

    New MacBooks

August:

    Announcement of new iPhones

September:

    New iPhone launches
    new iOS launch
    new macOS launch

October:

    Announcement of new iPad Pros

November:

    New iPad Pros
    Black Friday and Cyber Monday sales

December:

    Christmas sales
Last modified 2yr ago