Here's the challenge

Why is this difficult exactly? Just asking. Fly if out a mile, land it, then takeoff and fly back? What's difficult about that?

It's not difficult, if you know what you're doing. Of course there will be plenty of those who don't realize what they have to be careful of. Line of sight isn't the only thing to be concerned about. Uneven terrain, unleashed pets, etc. would also be on my mind.
 
It would not be possible here, thousands of trees and hilly terrain, at ground level you would lose LOS real quick. I flew from my normal take off point to my house less than a half mile away at 150' with full signal. My spouse was in the back yard so I started a decent to video her and by the time I got to 40' the signal (video) was down to 2 bars, at 20' I lost viseo and control was at 2 bars, so up I went. When they say LOS they mean it. So unless you fly in the desert or to the other side of the lake this would be a chance to take a hike.
 

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