I would suggest using the Check in trigger instead of all those other triggers. In particular, the startup trigger almost never works unless the machine is hardwired to the network and doesn't use any kind of certificate based connectivity. I see you're testing it against what looks like an Mac mini, so perhaps it is hardwired, but I don't know.
Login/Logout triggers should work, but again, it kind of depends on what kind of network connection we're talking about. The enrollment trigger is only going to run once, when it's enrolled, just as the name implies.
The recurring check-in trigger is the one that will run at a set interval, typically every 5, 15 or 30 minutes (plus some random delay added on)
I can't tell from your screenshots what frequency you have set. Is it once per computer or something else?
