I caught a lot of flack for the difficult process of updating the extension last time I made some changes, so one of the things I've put a lot of effort into is making the extension more tolerant of things being done out of order, and missing dependencies.
If you're updating to the newer format for the extensions (as of about a month ago now?), as an example, a user might first enable the Data Structures extension before enabling Dialog. Previously, that would cause an error, some annoyance, maybe even data loss. Now, instead, it loads all the information up as "unknown" types, and waits for other extensions to be enabled to try understanding what it all means.
I've also made sure that the transition from a monolith style object to a bunch of smaller plugin objects will be as smooth as possible, so users won't have to make any changes before things work.