Round Win Loop - I need to fix my map logic

I don't have any specific answer (I'm not too familiar with Arena logic), but have you tried checking the console on round win/loss? (Use "host_timescale 0.2" to slow down the server when this happens)

There are I/O debugging commands that show you the I/O happening. Try those.

Yeah, try ent_fire while in the game and test out individual entities, try firing the counters and just see what happens and eventually you'll be able to eliminate your options and get a conclusion

By "debugging commands" I would assume you mean typing "developer 2" into the console (without the "). You should try this, it shows you everything happening in the game at the time, and is very useful when testing game logic.

That's not enough to debug I/O. You need to manually turn on listing which Inputs and Outputs are happening. You can even step the I/O!

So give us the commands, henke.

it looks to me like you copied those game_text, math_counter, game_end, t_c_p_master and game_round_win entities from the example CP map that comes with the Source SDK content. You don't need those for an Arena map. All you need is a tf_logic_arena. The victor is chosen automatically when one team is wiped out, and if I'm not mistaken, a 'Sudden Death' (draw/humiliation usually followed by a round reset) event is triggered when the round time runs out and players from both teams are still alive. The round time is handled by a server cvar, tf_arena_round_time and the capture point unlock time is controlled by the tf_logic_arena. Capturing the CP will automatically choose a winning team, too. Try hiding all the entities I mentioned, except tf_logic_arena, saving the map and doing an entities-only compile