The water that sits in the area under the cabin step that the pump can't pump out is what I'm talking about. What do you guys do? Leave it or dry it up occasionally? Will it hurt anything?

I would shop vac the bulk of it out. Standing water is never good

I know it sound's ridiculous but I bought a pump type suction pump on Ebay for 20 bucks. I leave it in the boat. When I put the boat away, I put the hose down the sink draink and pump any water out that may be there.

I solved my issue by never letting the bow be low on my trailer always leave it with the trailer high in the front.
Rich

dont let the deck of your boat get wet. water comes in around the bow railing bases. it will never get wet if you do not soak your deck. Leave the step open so it evaporates or it will rot out the floor. Leave your back seat open to so it can evaprotate the engine bay and floor etc

Thanks guys for the advice. I guess I'll keep doing what I do. Occasionally take a shop vac to it. Keeping mine bow high will not pump all my water out. I trailer my boat to the lake on the weekends. Sits behind my houseboat while I'm there so if it rains not much I can do to keep it dry if water can come from the bow rails. Wonder why the water doesn't drain into the bilge?

JT mine is a 32 so on or off the trailer my bow is high and drains to the stern.
Rich

Hmm...
I had a 29 and now a 27. Neither drained to the bilge. Trailer jack is all the way up and doesn't drain to the bilge that way. Maybe if I put a board or 2 under it and get it higher?
I never liked using my cooler in the 29 for that reason.
I know 32s sit way lower in the water.

Had this problem as well, ended up taking the rails off and caulking the chit out of them and problem solved.

Soldier I forgot I did the same to my rails but the last time it went into shop for repair they left it low in the bow on the trailer and I had water again.
Rich