Tim Hunt

Moodle upgrade should always keep all your existing data.

The only reason that might fail is because doing this is sometimes complex, so there are occasionally bugs. Therefore, it is prudent to back everything up before you start, and know how to restore that backup. Then, once the upgrade is complete, have a poke around to make sure everything looks OK.

(1.9.19, 2.2.6 and 2.3.3 are all very stable, so other people have probably found all the bugs by now )

The recommended route is

1.9.x -> 1.9.19 -> latest 2.2.x -> latest 2.3.x

Note that 2.2.6 and 2.3.3 are due out next week.

Once a plugins has been submitted to the plugins database (https://moodle.org/plugins) it is now possible to translate it using the tool at http://lang.moodle.org. (This only became possible recently, but it is now the easiest way to do it.)

I think the situation people are worried about is with many user profile fields (~20?) not just 4.

Which version of Moodle? Since Moodle 2.1, the Essay question type supports attachments.