[whpalmer4]

I've seen a similar failure on the Mac, and wonder if the root cause might be the same. Those custom icons travel in the database just like attachments, and I occasionally see a failure (on the Mac) after syncing where OmniFocus loses the ability to look at attachments. Sometimes I lose the custom icons in the toolbar, sometimes not, but the database itself is not damaged, as syncing it to a new device shows the attachments and custom icons are fine.

So, next time you have your custom icons go "poof!" on the iPad, try looking at an attachment before you reset the database or reinstall the application and report the results.