Sometimes at a startup you just don't have the resources to do everything. Upgrading to Rails 3 pays down their technical debt substantially and will help prevent interface bugs like the ones you encountered in the future.
This particular startup had VC money flooding them from all directions. The bugs are still there. One involves credit card access between users, the rest are trivial (the stuff you'd let a junior programmer handle). Upgrading to Rails 3 doesn't magically solve anything.
