Excellent work on the app. It's fantastic.
A nice work around to the uploading files issue would be to piggyback your existing email solution. So after posting a message you could show a little "Attach files" link which would show an email address to mail the files to (or open a mail client if that makes more sense).
How come? Mobile browsers don't support it (for security reasons?) or it's slow/eats up precious bandwidth? Or am I misreading you completely.
On the other hand, the HTML interface is a mime-multipart form and a file upload - it's only convention that says "upload images only" - and the mobile platforms are very particular about access to files on the device. iOS for sure won't allow one app to touch the files of another.