I'm no expert, but it looks like it can be done, though not in a single application
iPdf and the notes-png-painting of the iLiad deliver the first three tasks:
Quote:
freehand paint / writing
multiple pages
annotate pdfs
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saving the created documents is something I currently am working upon. Merging a PDF with its scribbles is possible with Python

it is pretty slow though.
Unfortunately I ran into a wicked filesystem problem on my iLiad, needs to be reflashed by iRex :'( - NEVER name a folder with something like 'merge' or 'scribble'!
I cannot confirm, that it will run on the iLiad, but it very much looks as it could. I only had made one very little test that returned no issues.
Concerning bluetooth i have no idea, maybe one can access a bluetooth usb dongle as serial device like a usb-keyboard, via wlan the standard delivery service to a shared folder is always available, or you can use my email-client for this task. I'm think it is possible to code something similar for other transfer-protocols such as ftp with python.
Nergal