Frustrations with migration

I'm in a really weird headspace right now and I can't seem to focus on anything else. So I figure I'll leverage the Zeigarnik effect and write my thoughts down so I don't keep thinking about them.

The gist of my situation is that I just got a new iPad and also just erased my personal Macbook device (I'm using my work one as my primary device for now) so I was entertaining the possibility of actually getting a proper iCloud setup this time, instead of the complex Google/Apple/Microsoft setup I had on my old device, which still exists on my iPhone. I went ahead and created a new Apple ID and logged in on both the fresh devices and started playing around, to discover that iCloud sync is much better than I have always assumed.

However, thinking further into the future with the other services I would require, I started to reconsider the decision to start afresh, as there is a lot of data I would have to migrate over. Data like contacts, shared calendars, mail, etc. are all annoying to export and re-import. Logging in to my old accounts on the fresh devices would ruin the whole point as well. The staggering number of decisions and tradeoffs I have to make when setting up these devices is crippling my ability to do anything else now.

To add fuel to the fire, Apple just released the developer betas for macOS Big Sur and iOS and iPadOS 14. I want to try those out as well. These distractions are all making it extremely hard for me to concentrate on anything right now, and my productivity for today is pretty much nada.

I can't decide on how to handle the following things:

  • Shared calendars (Most people use Google Calendar not iCloud Calendar)
  • Password management (iCloud keychain is only accessible on Apple devices, no web interface. 1Password requires the secret key which means I can't log in on other devices)
  • Email (How to handle email going to my old email addresses. Configuring forwarding or aliasing ruins the point of starting afresh)

Gah this hasn't helped. I still feel confused and frustrated that there's no solution that just works. iCloud works but it's too limited within the Apple ecosystem. Google works but it doesn't tie as well into Apple hardware and it has major privacy issues. Everything else just isn't comprehensive enough. I'm frustrated that after so many years there still isn't a good solution that works for everyone and with everyone.