1. For some reason, heli hasn't spawned in at all for about a good week now. I have a Barren server with 40 people on it average, it should be spawning in just fine. All my plugins. The only plugin i can think of, that may be messing with it, is TimeOfDay. Instead of going through night time, it automatically becomes day at a certain point.
     
  2. Have you tried removing the TimeOfDay plugin at least for a little while to determine whether or not it's at fault? That's definitely something I would try, especially since you already have an inclination that it may possibly interfering.

    Aside from that, I would have to guess it's one of the plugins, if not TimeOfDay.