Debugging A Logic Case Entity - Need Help

I'm currently attempting to cause the map, on round start, to generate one of several sets of props. Here's how I'm doing it:

logic_auto
Output1: OnMultiNewRound clear_props Trigger
Output2: OnMultiNewRound section_1_props PickRandom (delay 1 second)

logic_relay 'clear_props'
Output1: OnTrigger prop_* Disable
Output2: OnTrigger prop_* DisableCollision
Output3: OnTrigger prop_* DisableShadow

logic_case 'section_1_props'
Output1: OnCase1 prop_1_1 Enable
Output2: OnCase1 prop_1_1 EnableCollision
Output3: OnCase1 prop_1_1 EnableShadow
Output4: OnCase2 prop_1_2 Enable
Output5: OnCase2 prop_1_2 EnableCollision
Output6: OnCase2 prop_1_2 EnableShadow
Output7: OnCase3 prop_1_3 Enable
Output8: OnCase3 prop_1_3 EnableCollision
Output9: OnCase3 prop_1_3 EnableShadow
Output10: OnCase4 prop_1_4 Enable
Output11: OnCase4 prop_1_4 EnableCollision
Output12: OnCase4 prop_1_4 EnableShadow

Here's the problem: I ran the map and everything worked fine- it disabled all props and then the logic_case picked case #4, and those props were enabled. Then I disconnected, created server, and it picked case #4 again. Disconnected again, created server, and this time no props showed up.

All names except the wildcard were grabbed from the dropdown menus, so this isn't a typo problem. Each set of props has its own world model, so I know for certain what case is being triggered. Prior to round start as I pick team & class there's flashes of the screen and I can see props from other sets present, so I know they're in the map at loading.

I'm intending to go back and alter things to try and clean up the logic_case (by having each case trigger a logic_relay that has the set of 3 enables), but before I do that I'd like to figure out what's not working here. I can upload the .vsf if that would be helpful.

Actually each case used multiple instances of a single prop- Case1 spawned swarms of traffic cones, Case2 spawned cement blocks, Case3 spawned dumptrucks, and Case4 spawned stacks of train wheels. After multiple reboots I established I could get everything except Case1 to appear, and I was getting blanks for that one. So I replaced it with oil drums. And lo, after another 12 iterations or so, I had oil drums and no blanks.

Lesson for the day: traffic cones break logic.