As regards the connections - I'd use a DECENT crimper (one of the ones from around $100) with decent heat shrink butts. That will be extremely strong and waterproof. A lot of people then put the connections in a junction box. Make sure they are as high out of the bilge as you can!
It may be worth getting an additional small automatic bilge pump (rule does a 500GPM one) and mount that right at the bilge bottom, with a check valve or a downsized outlet. That way it will take care of any nuisance water, while your other (hopefully vastly bigger) bilge pump will handle any major water ingress.
It may be worth getting an additional small automatic bilge pump (rule does a 500GPM one) and mount that right at the bilge bottom, with a check valve or a downsized outlet. That way it will take care of any nuisance water, while your other (hopefully vastly bigger) bilge pump will handle any major water ingress.