Easiest way to send updated program to multiple units?

We are using VS 2008 to write a fairly basic warehouse program for our Zebra MC2180 units.

 

We have 5 units, so if we write an update to our software we have to rather laboriously plug each unit in and copy/paste the required files across...

 

Can we not push an update to them over wifi? Can we setup a shared folder perhaps?