Thanks, Preach, at least now I understand the problem.

I don't like the approach with a huge trigger, but you gave me a few ideas. 

Hope this hasn't been asked before, but I've been Googling for like 30 minutes so it might just be time to ask. I've been trying to make a Quake 1 map in TrenchBroom for Arcane Dimensions which takes place mainly on a giant elevator, and whatever entities I put on top of it seem to just not receive any light, even though the brush itself is being lit just fine. So if, say, I've got a point_light angled straight down over an item_health, the func_train underneath it receives the light, but the item_health remains entirely pitch black. Is this something that can be solved, or just an unfortunate quirk of working with func_trains? And if so, is there any kind of hack I could use to get around it? I've wanted to make this big elevator map ever since I first played the finale of ad_necrokeep, and I remember there being a normal-looking armor2 on the platform when that section starts, but I've had no such luck. (For what frustration this problem has caused me, I will say that fighting pitch-black monster_skullwiz's looks very cool.) 

The entities take the light value from the "ground", which is the worldspawn (level's static geometry). Stuff like trains, doors, buttons (func_#### and similar brush models) aren't considered "ground" because they aren't worldspawn.

This video should help:

https://www.youtube.com/watch?v=u8-mw79NGDU