What differences am I likely to care about if I use self-hosted versus cloud for JIRA, especially with regard to customization.
I've been a JIRA and Confluence user/administrator for many years. I started with self-hosted and have become very comfortable with customization of fields, screens, state transitions (workflow), notifications, hooks, etc.
With each client, I typically start a new JIRA instance from scratch and customize to their needs. I am not talking about moving an existing JIRA database, but am deciding whether to start my next client with a self-hosted or cloud JIRA version.
I also care about Confluence and BitBucket, but I've typically done far less customization of those.