Also check if the watchout server runs smoth with arena, I had a story were the watchout machine doesnt at all liked resolume and it was soo slow and bad i couldnt use it. The parts were powerfull but somehow the watchout setup made it impossible.
I dont understand it 100% but i think what you are looking for is autopilot? Crop the first file to the point you want to switch, set autopilot to "play next clip" and transition to 0.
The whole idea is for me to set up a range of different clips, hit go and then disappear to the dance floor for 6 hours whilst all this stuff just plays by itself. Sounds like a DJ not a VJ lol https://resolume.com/support/en/clips#auto-pilot Auto Pilot is what you're after. If you want random part...