Hi Zach,
Viewing successful couples as a Bull, I’ve noticed that the long term couples seem to communicate and take it slow (at first). You seem to be doing both.
Watching cuck or HW porn together is a good starting point. Discussing scenarios and role playing while you’re in bed is also good.
The next logical step (which you have already suggested) is to chat with a few men on a dating site. Either her alone, or together as a couple. If she is chatting alone, she should share the conversations with you (and let the guy on the other end know that as well).
If she is feeling comfortable with that after a while you can then see about meeting for a drink (alone or together).
Just a note of personal history. I once chatted with a very hesitant wife (the husband was very eager) for almost a year before meeting her. But once she got past her initial reservations she became an incredibly sexy and sensual hot wife.
Good luck, and I hope you have some great adventures in the near future!