Now is the time. Washdown and live well can share the same through hull. Either T off the sea cock, or get a pump that offers fitting. You definitely want a sea cock and access to use it Either Marelon or bronze are good. Avoid un reinforced plastic and stainless. Stainless is great above the water line, but below, you’ll be fighting rust stains. A scoop style strainer facing forward will assure that you gave good flow enemy at speed.