Welcome LiveBootleg. Can confirm that water is very unlikely to be an issue at that time of year and after all the rain this year. Remember to fill up before ascending passes that follow ridges (like Grays and Organ Pipes).
What exactly do you want to see at Ships Prow, do you want to do the pass or see the actual Prow? If you are intending to do the pass, bear in mind that it is long and tedious. The Prow looks best from below - problem is to get there you may as well do the pass then since there aren't any others very close by.
The KZN Wildlife gates open pretty early, 6am I think, maybe even earlier in summer. Phone them and check.
Security: Grays, Tlanyaku and Organ Pipes Passes are major smuggling routes. Though they generally leave hikers alone, do not leave your stuff unattended in this area unless it is extremely well hidden and you haven't been noticed. Avoid moving around in the dark since they can mistake you for a patrol. Be prepared to hear them moving through at night, even with occasional gunshots. Keith Bush Camp is still OK cause its a little off the trail, but don't camp at places like The Neck, and the top of passes as Aux mentioned. Don't use Nkosazana Cave, its likely to be wet, and it will be peak smuggling season, so they will make use of it too. Its a great cave for the winter.