Sam, that rod holder spread is awesome and they look like they will have plenty grip. It's going to be a wet ride for the gear, but the tramps will help.
As for the sail rigging, I have only had minor mainsheet issues with the built in rod holders (non extended) so I think you are very safe anywhere out on the rear Akas. The only exception is when the sail is luffing violently and the loose sheet is swinging around. (If that happens, watch your noggin too).
If you're headed offshore, you'll want to keep a close eye on the outboard reels. Swells are going to kick up under the windward tramps and want to unseat things. On the leeward side, the Amas are going to occasionally bury and there is a risk of washing the poles overboard or even burying the tips if they are too horizontal. Easy to snap a pole that way.
Picture the boat being rocked by a good wave or gust while there is already pressure on the line (from a large bait or fish strike). That's the minimum angle you want to go with. Lock that in and your expensive gear should never become a "water brake".
Would be a good idea to buy more phone cord though. I did.
BTW, that Hobie live well looks awesome. Did not know they came in yellow trim! That's one lean mean fishin machine.