Follow up question then. If there were a way to run it seamlessly, same level of effort as Trello.com would people do it?
There are some pros to the paid/hosted option that can never be replicated by self-hosting:
- someone else handles crashes, bugs, and other emergencies - economies of scale (large, purpose-built operations with costs shared my many customers) - free (or cheap) customer support
The biggest reason I see people moving to self-hosted options is to keep their data private.