So, it is a whole bunch of moving parts.

This is work that my company, ADR Advisors provides. You are in the classic case where they can use CIO/CTO help, but are too small for that. We provide these services the same way that a small company uses a lawyer or accountant outside their firm. The idea is to to provide the IT managing resource (you) with planning and vendor selection support that is fast, lightweight, and not affiliated with any particular tech vendor. Please let me know if you are interested in this assistance.