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There may be multiple reasons behind not having a messaging system on top of Steem. There was one that was developed but I believe it is discontinued now. It was named mongosteem if I remember correctly.
The entire Steem blockchain is publicly available for everyone to see. This makes making a monetized messaging platform impossible. Private messages are expected to be private, that is, private messages should only be accessible to the sender and the receiver.
But since Steem blockchain is public, all of the messages will be available to the public if they are posted in the Steem blockchain. This is why mongosteem was shut down. it is not viable to make a messaging platform on top of Steem.
Another option is making a messaging platform using the encrypted memo feature of Steem. But this has a problem. Cause both the active key and the posting key doesn't give permission to view encrypted memo. To access encrypted memos, users need to use their memo private key or the master password. This could cause security issues.
If more and more people use the master password to login so that they can use a messaging platform, then it could make them sitting ducks for hackers to steal their funds. But using the memo key to access the messages will make things harder for the average user because they will have to enter two passwords to access their messages (login with posting key and then use the memo key to access the messages).
This is surely going to annoy a lot of users. So, based on these considerations, it is a very difficult tusk to make a messaging platform for Steem that is easy to use. Also, it will require a lot of hard work as well. Steem Inc devs are currently busy with SMT's and hardfork 20. After they launch these two important things, they might start working on a messaging platform. That's just my speculation though.
