Well one problem I'm seeing already is that you have two team_round_timers set to appear on the HUD, when you can only have one on-screen at a time. Another issue is that your map is
broken as shit. It causes VBSP to crash with a bunch of errors I can't be arsed to fix, so I can't even test anything. And this is with
just VBSP running.
Anyway, one thing you could try is unchecking the "Fire Once" box in the output that plays the audio clip. Generally I've found no reason to have it enabled 'cos it tends to break things.
Also,
w h y
EDIT: Actually I'm going to reiterate what everyone else has told you: stop working on this map and instead make a new one from scratch. You really shouldn't mess around with full, ready-made products until you understand how Hammer works, especially since this is your first ever map. Once you've got more experience then by all means revisit this project if you wish, but trust me when I say that continuing on with it now is gonna be nothing but a bad time.