is your bilge pump original ??
until you answer that we can't give you good guidance,
The best guidance for a rookie is to know YOUR boat, there's no telling what a previous owner might have done,
my 2007 the bilge power is a on the dash, when powered on, it cycle's every few minutes and if it senses water (increased pressure to turn the pump) it continues to run until the resistance (water) is gone,
on my boat if I listen closely without the engines running I can hear it cycle,
I ALWAYS power the bilge before cranking the engines to off load from the trailer and never touch it again until the trailer is out of the water,o
One time we rented a cabin and I turned the bilge off over night figuring the only water intrusion at that point would be through hull fittings which is very minimal seepage, I did check it after 4 hours and found it still dry so I felt relatively comfortable for the nights,
Jet boats use lake water for cooling, if one of your cooling lines comes loose it a short trip to having a sunk boat as more power means more water dumping into your engine compartment and if you driving you may not notice the bilge working,
2 suggestions,
1. a secondary bilge pump located at a different level so if you see that one working you know you have an issue,
2. a high water alarm, these are really inexpensive and could give you notice if you loose a cooling hose underway,