Installed the latest version of the plugin earlier, and after restarting the server, used voteday until the plugin itself tried to spawn a Chinook. One spawned, flew around the map, dropped a crate, and left. Everything seemed like it worked fine.
Until I came back a few hours later.
I currently have 5 chinooks on my server, in various locations, with no AI, sitting on the ground. Several are underwater. There is also one active which is flying around the map correctly, for a total of 6 chinooks. I am unsure if they just aren't despawning correctly, or something else is going wrong.
EDIT: For the record I don't really have any plugins that would modify the AI or mechanics of entities on my server. The map size is 3500. I have some screenshots I took of the map.
https://i.imgur.com/Fs6MEER.png
https://i.imgur.com/XGnfJWt.png
That chinook I said was flying around correctly? Left the map without dropping a crate.