Re: adding bilge pump to boat that never had one?
bailing depends on how much water is held inaccessible under the deck. Anyway, every boat should have a bailer so I hope you aren't adding that.
True, older boats didn't have electric pumps. So if you have to keep the boat original, for example, for boat shows, then there are ways to reduce risk, other than leaving it on the trailer.
Pumps have two purposes, so you may want two pumps.
Purpose one is evacuating large amounts of water in a swamping, etc. Go back to your grandfather's rig: install an electric in the bilge, run the hose over the side, but when you aren't using it, just leave the hose stowed. I do that with my back-up. Just be sure you can deploy the hose quickly, and you have a clip on it so you can secure it overboard.
Purpose two is getting rid of small amounts of water that accumulate, as to maintain a dry boat while moored, etc. (water in a day trip won't matter). In older boats you just pulled the plug and ran it out. But one of the best devices is a hand pump--available at boating stores everywhere. You can stick it inthe bilge hole and in a few seconds dry it out. I remember a waterman had one mounted on his transom so he could give it a couple of pumps as needed. I carry one on each boat as a back-up to the battery-powered pumps.