Suspend MVP frugality for a moment. What platforms scale best for training people, TCO, security, etc as you grow from 3 people in one office to 350 people in 12 office locations and more remotely?
Machines, servers, phones, productivity, groupware, crm?
Founders with successful exits, what IT regrets did you have along the way?
My advice -- keep it simple. Read http://highscalability.com for stories on how others did it -- see YouTube for lessons on simplicity.