I think the traditional model for a monastery is destined to fail in the West unless there's a huge upsurge in formally adopting Dharmic knowledge systems (even that is unlikely because they're seen as identity-based 'religions' rather than vehicles to increase the consciousness-level of civilization).
I can only think of Osho's failed attempt, but the Vipassana movement and the growing number of farming co-ops look like incredible success models. Though these aren't really monastic at all, they provide more holistic and conscious models for human life *from which* perhaps small clusters of real, serious spiritual practice can grow out from.
I am honestly wondering if I have the capability to start anything of my own! Perhaps if my spiritual practice reaches a state of irreversibility. There's a prayer I read in a Buddhist text called Akshayamati-paripriccha-sutra that was a prayer, 'may we never hold positions of any influence until we have totally conquered our afflictions and anger!'