George,
Letting users send email from your mailserver or a mailserver you use is not a good practise and I believe the issues you see will be standard before to long (i.e. it won´t be possible to send email like this any longer). Another thing, when sending like you do, you are very likely to be flagged as a spammer which will severely affect you, your app and even your users negatively (mailservers, mail hosting providers etc. look at IP and other things when looking at things like this and if they see a lot of mail coming from your server IP etc. when using this sending "mechanism" (i.e. send from whichever mailadress), they will most likely flag you as a spammer).
I think better email handling (multitenant) is REQUIRED in Aware IM. In today´s world, mail is absolutely crucial for web apps and having this / a proper solution for this is very important. Support, hope you see this comment and add this to the roadmap. Another very important thing is Google Calendar sync (multitenant). That´s ALMOST as important (not quite) and having a good working calendar sync to Google will enable lots of additional uses/syncs etc. from Google. Thanks in advance.