If not for the camera improvements and the Dynamic Island, I won't be upgrading this year. Getting a new replacement iPhone always make you decide whether to start with a clean slate or migrate from your old iPhone.
I have been itching to start with a clean slate, but my Apple Watch streaks make it difficult to let go (1656-days daily Move streak!) - so migrate it is. One of these days I'll drop this streak obsession and nuke that iPhone!
With the iPhone 14 Pro, the first thing to do is to update it to the latest iOS 16.0.3 before starting anything (this is a personal preference, though). Whilst updating the iPhone 14 Pro, make sure that your Apple Watch workout (assuming that you have completed the 30-minute workout ring, of course) is reflected on the old iPhone already. This ensures that when you back-up your iPhone to your computer, all data is intact. I had an experience before when I forget to check and lost a day's worth of fitness data.
Do an encrypted back-up of your iPhone to your computer - make sure that it is encrypted, otherwise you lose some data, like WiFi passwords. Two years ago, I'd unpair my Apple Watch before the back-up. Restore the back-up on the new iPhone and pair the Apple Watch with the new iPhone.
Apple made an entirely magical migration experience last year (or was it the year before), where you just put your iPhones side-by-side and wait a couple of minutes, and voila! The new iPhone is ready - just transfer the SIM and that's it (Apple Watch pairing gets transferred, too!). My migration process from iPhone to iPhone was uneventful - took less than 40 minutes to migrate and download the apps from the iOS App Store.
What did not migrate is the eSIM (I have Globe eSIM, since Smart's eSIM is limited to a select type of subscribers only, and worst, Smart people are saying it is not yet stable!) - Globe does not support the eSIM Quick Transfer as mentioned by Apple <"https://support.apple.com/en-us/HT212780">, so, like before, a visit to a Globe store is necessary to get a new eSIM QR code (bummer!). Now that I have the new iPhone 14 Pro setup and ready, a new encrypted back-up to the computer is the next step - doing it now as I type this. Remember to always have a local back-up. If you got yourself a new iPhone 14, how did your migration experience go? Surely would like to hear from you.