For me, i started with an iPad Air first
iPad Air (2021) as just wanted a established tablet brand while holding on to my Pixel Phone
iPhone 15 Pro Max ( Oct 2023)
Apple Watch (Oct 2023)
Apple Airpods Pro 2 ( Nov 2023)
Apple TV 4K 3rd Gen ( Nov 2023)
Probably will get a macbook air late next year
2004 - 2009: A variety of iPods
2010 - iPad
2012 - iPhone 4S + MacBook Pro
2013 - Time Capsule + Apple TV
2014 - iPhone 5S
2015 - iPad Air 2
2016 - Apple Watch 2
2017 - iPhone 7
2018 - Apple Watch 4
2019 - iPhone XS
2020 - AirPods
2021 - iPhone Pro 13
2022 - iPad mini, AirPods Max, MacBook Pro, Apple Watch 8, and 4 AirTags
2023 - iPhone 15 Pro
I was doing okay with a steady stream until all hell broke loose in 2022 and I had to replace a lot of stuff. My bank account is still recovering.