When the waters gets to your neck, it's time to swim for it.... But more seriously, if your pump is cycling on a regular basis, it should be looked into.
I'd break it down into two different categories. Water that gets into the bilge by design, and water that is collecting there due to leaks.
By design, I think the most common is a shaft packing gland. They are intended to drip. Other sources could be condensate from HVAC systems, and even gray water from showers and sinks. It all depends on how your boat was set up. Gray water should really go directly overboard if possible, or into an enclosed sump and pumped overboard. In the bilge, it will stink things up. If you have a packing glad for a shaft seal, then the bilge will be wet, and adding a bit of condensate isn't a big deal. But if you have a dripless shaft seal, then I'd want to condensate collected like the gray water, and I'd be looking for a completely dry bilge. This is my personal preference - completely dry. If nothing else, it makes it clear when you have a leak.
As for leaks, RSN48 provided a good list of candidates.