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Yeah, it can be done with appropriate scripting. You can try looking at the co10 Escape mission for an example of most of what you're looking for — in /Code/functions/Server/fn_RunExtractionHeli.sqf. (Note that some of the variables have "boat" in the name even though they actually refer to helicopters ... the script was originally adapted from an extraction by boat and they never bothered to change the variable names.) At the end of the mission, the players pop a smoke in an area which triggers this script to run; it spawns in two transport helos and an attack helo escort. The two transport helos land near the smoke and then the mission waits for all living players to get into a transport helo. When all players are on, the helos spool up and take off and the mission ends. It doesn't cover moving the players to another location but that should be a fairly straightforward task once you are familiar with how the rest of it is scripted.