Hello and thank you for your interest in the project!
Any documents sent with Bob is encrypted 
. What we don’t want to do is infer the MIME type of what the user wants to send - in this we are not trying to introspect the content of the document. The trade-off is that we can’t infer whether it would make sense to compress the document or not. For example, a user might expect Bob to be smart enough to recognise the document as a video and, in that case, not compress the document. This is not the case, however, if you do not want to introspect the MIME type of the document to be sent.
In other words, the user must be aware of what is trying to be sent and use --no-compression or not accordingly. Again, the latter option does not override the encryption .
One of the improvements we want to make is the ability for Bob to actually do “peer-to -peer” - and not go through the relay. However, we would like to keep the default of using the relay for simplicity. The peer-to-peer case probably requires a network state (open ports, accessible peer) that many don’t have for various reasons - conversely, we know that it is possible for the user not to have access to our relay (but to have access to the peer) and it is in this case that we would like to do true peer-to-peer.