Finding time to meet with all those students in a meaningful way must be a challenge that will only get bigger. I am familiar with a school that has created student groups to accomplish some of the transition related things you have identified. When a new student enrolls they are assigned to one of these groups and is a member until they graduate. The school has advisors to the group and also has activities that are group based - best quarterly attendance, best GPA, community service projects, etc. The students select their own leaders, who in turn work closely with the advisor. The system provides for an open line of communication and creates spirit among the members. Would something like that work for you?