How to Find the Right Contemplative Community

A reader named Brian writes:

Being a Lay Cistercian seems to be an important part of your journey. Im wondering if becoming an oblate is a next step for me?
My spiritual director and I have discussed this off and on for over a year now. While I have an established contemplative practice (e.g., Daily Office, Lectio Divina, Examen, Centering Prayer), he and I agree that scaffolding helps keep me intentional, accountable, and engaged with community.
How to discern which monastery to affiliate...