I would tend to agree with those calling for a migration to WMF while they have resources available rather than delaying the migration. We obviously don't want to announce to the world that the new site is up and running if it isn't ready, but if we simply transfer hosts without any major announcements and include site notices that state something like "Help tag/transfer xx,000 images so that Wikivoyage can complete its migration to Wikimedia!" then we may attract experienced help from other Wikimedia projects who read WMF mailing lists and can assist with the process, and we'll also begin getting them familiar with Wikivoyage in the process. Meanwhile we begin benefiting from WMF hosting, software updates, shared infrastructure, shared user accounts, global spam blacklists, etc, etc.
In a perfect world there would be unlimited resources to ensure that everything is transferred flawlessly and the migration is done without anyone noticing, but in the real world it seems (to me) to make more sense to complete the migration while WMF has technical resources available who are focused solely on getting the new site up and running, rather than holding off until a time when we may not have the same resources at our disposal.
My two cents.
Ryan