I wouldn't worry about a 5' elevation difference, but if it turns out to be a problem, you can always add a pressure booster.
There are a number of ways you can do this, but the thing to keep in mind is, you want ONE controller. You can have as many pressure tanks as you want (in theory) as long as the pump can handle all of them.
And think about maintenance and think about potential problems. You want to make sure you can isolate both buildings (that means valves) and you want to make sure a burst pipe in one place doesn't drain the whole system (that means check valves). You also don't want a flushed toilet in one house to mean a cold shower in the other.
Maintenance is the reason I don't like a pump house located near the well head. You'll have to run power there, and you'll have to do maintenance there. I'd rather have it in a comfortable basement with lots of room. But... it IS a very workable solution.
Another approach is to forget the pressure tank. Pump to a storage tank, and then have separate pressure boosters to supply each building. This isn't as common a setup, but it has a number of advantages. For one, much less load on the pump. It also eliminates any problem with elevation differences, and one building affecting the pressure in the other building.
These folks show a setup with a conventional pressure tank after the storage tank, which is one way to do it.
Water Storage Tank Systems | Texas Water Services and Well Drilling
Since you are in the high desert, the advantages of this should be obvious. In case of a power failure, you still have water to drink for a while.
Whatever you do, go bigger than you think you need. Pump and tank and pipe sizes. You will be glad you did.