Andrew,
It sounds like you've thought through your areas of possible resistance and have a plan in mind. One of the things we've done is to gather alumni success stories and then used some creative ways to share them (ie: alumni success story posters, pamphlets in the lobby for prospective students, alumni success story books, 'thank you' emails to staff/instructors, etc.) There is nothing like the power of a 'story' to encourage staff and recruit potential students. Reminding your administrators and corporate employees that every alumni is a walking, breathing advertisement for your institution, it may help them grasp the benefit of spending a little time and money on them.
Good luck!
June Gudeman