If this is "your" ArcGIS Server, take advantage of caching any of the static data/services you have and send them a copy of the cashed folder...the speed of access for ArcMap will be much faster than accessing thru services, whether AGS or AGOL.
Can they checkout any of the data for offline use? Check-in/check-out operations for those things that they are editing....easier done, I think, if you have ArcSDE with versioning, but if they are off your network, access might be limited or have more hoops to go thru.
Keep the data that needs to be pushed back and forth to a minimum, maybe after the first month of getting things setup. I agree with Joshua, might be best to get extra, or check out what mid-month bump-up costs are, at least until you get the feel for usage.
I think more than the data usage issue, the speed via a satellite connection is going to be the most frustrating thing for you if heavy data isn't local. We still have offices that are frustrating slow, especially after having reasonable speed at home/office. So, question is how can you make that tolerable.