1. No, only tasks/process instances currently. I've added that to our 1.4 backlog
2. That is done by some custom code in the share connector. For files, you need to upload the file, and you can use the id you get back to populate the variable on the form. You can also pre populate the other values, but you'll have to resort to some custom coding (one way would be to use the javascript extension mechanism, see the docs section on it).