I had a similar situation on my old Catalina 28. Similar pedestal and cover over the steering gear setup. The Catalina also suffered from a poorly engineered joint between the pedestal and deck where water could get in and penetrate the core.
There are two things that I'd want to know about the problem you're having.
1. Is your core involved? If that vertical section, and the immediate surrounding area doesn't involve the core, then that would greatly lessen the severity of damage done by the water intrusion.
2. Where is the water going? On my Catalina, it dripped directly onto the aft berth cushion. Not good.
So, if you don't have a core issue, and if you're LUCKY, the water is finding it's way to the bilge without doing any harm, then you can avoid making a major project out of it. Cuz that's a tricky situation you have there with the runoff from the drain channel cascading directly on the cable bundle. The water gets inside the bundle of wires and sneaks in that way. Ugh.
So, if the core is safe, and the water's going to the bilge, I'd go with 3M 4200 or it's equivalent. Practical Sailor gave high marks to Loctite's sealant as a 4200 replacement, and it costs a LOT less. I got mine at Home Depot. Hopefully, no one used silicone around that bundle, as the new, proper sealant isn't going to want to stick anywhere there was silicone. But you knew that.
It's been my experience that relying on sealant to seal tends to be ineffective. It works best where the penetration has been engineered to deal with the water intrusion, and the sealant just provides insurance. That penetration was engineered to be a train wreck, so as you suggested, you'll be renewing the glob occasionally.