Drill the hole as small and high as possible, caulk on both sides and use a small stainless “shield” to guide and protect the cable around the hole. I’ve had this in place for many years with no issues.
Five years for risers and manifolds on a salt water-located lift. I flush religiously. You need a sinking fund which prepares you for the five-yearly bill.
I agree with the advice to apply elastomeric roof coatings, but first I recommend a rather tedious session with a good pressure hose. This should relieve the underside of the carpets of all the loose rubber. Allow to dry thoroughly. Then brush a g...