Hi @bjasik and welcome!
To add an email to the daily Hello, Money email, using a forwarding rule is the way to do it. (For now: my initial response included a beta feature that allows you to add emails via the Tiller console, so I would expect there will be an official way to do this soon.)
There’s no official way to set up additional customized emails, but you should check out this show-and-tell @Mark.S put together:
Regarding private investments, there’s been some discussion of tracking them, e.g.,