I luckily have been successful in finding and fixing many surface water leaks on our 1994 sailboat. I am proud to say that as a result, my bilge has been bone dry now for years. Don't accept statements from old sailors that boats are always wet.
Most of the time, it has been easiest to be on/in your boat during a rain event and be able to directly see the leak source or track it back to the actual problem spot when a puddle winds up in an unexpected area. "Seeing" the source may require sticking your head into really strange and uncomfortable areas though. It may also take some interior disassembly (compartments, shelves, etc.) to see the problem.
Leak sources don't have to always be complicated to resolve. Also, many are caused just by ignoring to do simple maintenance. For instance, window leaks may be due simple to the latches. Disassembling and doing maintenance on the latches for some types/brands of opening ports/windows is simple. Latches may contain very small o-rings that seat against the window lens and are the things that keep water out. These o-rings dry out and crack over time, but an annual removal and replacement of these very inexpensive items, or cleaning and lubricating with a proper grease does wonders. Also, don't tighten the latches during reassembly too much. Let the o-ring have room to do its job. Flattening the o-ring due to overtightening will only result in early leaks and marring of your acrylic lenses. Then you will ultimately need to replace the lens too.
A leak in an original/old potable water line from my water tank to my head sink on the opposite side of the boat caused water to build up slowly in my bilge. Initially I was worried that I had a keel bolt leak. However, when my potable water pump kept cycling on/off, that was the key. I depressurized the water lines and gradually dried out the bilge helping to confirm my diagnosis. I ultimately had to replace the water lines. I was not able to remove the old lines because they were essentially held in permanently within a structural fiberglass floor/hull grid in my boat. Thus, I had to get creative to install/redirect new lines.