I suggested 14' minimum clearance because that is the standard used here by the utility for lines on a lot. It makes sense. You don't have to worry about tall vehicles like a feed truck, motor homes, a large load of hay, or whatever. It just becomes a non-issue.
I looked at this some more last night. I think I can come off the house at about 11' without putting up a mast and go all the way to the barn without an intermediate support, and attach to the barn at a height of 22'. This whole area is generally inaccessible to vehicles, but if I ever had problems with the well, the well truck would have to go under this wire. I will have to trim a few branches to make a tunnel for the wire, but I'm sure my wife will issue a tree trimming permit if she has to choose between no electricity in the barn and trimming a branch.