running wires strait uo transome through lip at swim platform

[sea ray den]

my sea ray sundancer 250 has a molded hollow lip that will bring wires into engine area at swim platform, im thinking of drilling a big hole for transducer cable and some led lights.
light were drilled below water line by previous owner and leaked.

 

[Augoose]

Welcome to the forum.
Measure twice, drill once, seal with good sealant, ensure you use proper gauge wire for your application and use a fuse!
Good luck