This is a great question. I've seen so many small libraries get in trouble with contracted techs in various ways, not because the tech is trying to cheat them.
Also the
Choose the Right Consultant article linked from the Finding article makes some very good points.
Trying to figure out their experience, and whether it matches your needs is very important. Techs will often push systems, products or ways of working because they are what they know best, but are often not what you really need.
And think from the beginning about what happens when this person is no longer working for you. Are they building arcane systems that only they can service? Are you making sure that they will be sharing all important and basic information like admin passwords, networking details, etc.?