Scenario #2:   At the top end of the tether, the skydiver could attach a kite to aid line retrieval. A complete separate 'chute might be carried so that the first one could be hooked to the line allowing a full skydive instead of just a rapid-descent mode.
~ BobS      M3247

1. The lifter wing stays flying after the skydiver releases into free-fall. Skydiver has a packed wing for opening after separation from the lifter kite system for a glide.
    
2. Maybe BobS' comment on the "attach a kite to aid line retrieval" is for first scenario, which see. 
    
3. I am not clear on meaning of "instead of just a rapid-descent mode."  Are you referring to the rapid descent of the main tether in Scenario #1?   Or are you referring to the rapid descent of the entire system; and in contrast the scenario of this page leaves the lifter system flying while the skydiver is separated?
    
4. This is a relative to early man-lifting kiting with the added aspect of dropping off the man-lifting kiting into a skydive. Close to this was the beginning of skydiving: The history of skydiving starts with Andre-Jacques Garnerin who made successful parachute jumps from a hot-air balloon in 1797.  But hereon now we are considering releasing from a KS with a mooring on the ground instead of a hot-air balloon.
    
5. This scenario branches on the nature of the mooring. Is the mooring a moving vehicle (car, truck, ship, raft, etc.) or is the mooring fixed (with or without payout winch). These split sub-scenarios have their own special design and operational needs. Use of ambient winds or the creation of artificial winds by moving moorings makes a difference.