At our HOA we are trying to drive behavior to use the portal for all communications. It would be good if in the Message Management that you keep all the conversations in the property record rather than send emails. For example, as a homeowner I send a message. There is no record that it was sent and so I have no idea if it was received or read. On the Admin side it would be nice to keep track of all the messages going back-and-forth, rather then shifting to external emails. Having all communications within the system would help in auditing of conversations.

At a minimum you should cc the person sending the message so they have a record that the message was sent. Otherwise it's just a black hole.