We try to predict when it's definitely going to break the circuit.
As you have noticed the amperage ratings on the equipment has some overhead built in. Experience will lead you to understand that adding up the rated current draw gives you some idea of what you need... but you also have some wiggle room.
Yes, getting a feel for that wiggle room sometimes involves having the circuit breaker pop. :-)
From a practical point of view... make sure you have all 15 or 20 amps on that circuit. Don't share with any lighting or beer coolers. Bring good quality extension cords and you can stage a loud bar band with out too much trouble.
I don't recommend lifting a ground... but you can sometimes lift ground and use a 2nd circuit without adding noise.
Sometimes you can use a 2nd power circuit because some devices are separated from the system. For example; Mic'd guitar amps that don't have a direct wired connection to the P.A. can be on a 2nd circuit.
best regards,
mike