Can't log into iCloud after Time Machine restore

For several years I've been taking Time Machine snapshots of my MBP and restoring them on my MBA to keep all my development tools and apps in sync. Recently I performed a restore and I'm unable to log into iCloud on the same user I use on my MBP on my MBA.

Through support chat we established that I can create a new local user and then log into iCloud, but this presents problems for me as all my tools and configuration would have to be copied over after each restore. Support chat and I were unable to identify the problem that was causing this and resolve it.

I'm curious if anyone else is experiencing this, and if so, has someone discovered a fix or workaround.

Thanks!