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Or you could use something like this https://ca.binnacle.com/Electrical-Cable-&-Deck-Connectors/c58_198/p10126/Glomex-RA140-Cable-Feed-Thru-White-Nylon/product_info.html
or this https://ca.binnacle.com/Electrical-Cable-&-Deck-Connectors/c58_198/p1381/Blue-Sea-1002-Waterproof-Cable-Clam-.825-in./product_info.html
I used that type on all cables coming out of mast side, different sizes  for different cables. Easy to attach.

I ordered the first item you mentioned. But now I am wondering how well it will hold up in the sun being that it is made of nylon.  Was it the second one you mentioned that you used?  If I were to use one of those, is there any danger of the cables chafing if the underlying hole in the aluminum is left bare?

Also I found that it's not easy to find the right rubber grommet that will fit the thickness of the mast cap.  I found some retailers online that can supply them in the exact specifications but they deal in large quantities.  You can't just go down to your local hardware store and pick one up, apparently.  At least that's what I've found.

Perhaps you could drill a hole that removes the problem area and install a rubber plug. Then grommet the hole for the wires and seal. We use big rubber plugs on old police cars when taking all the lights and antennas off.

How would one drill a hole that removes the problem area?  I assume you mean to enlargen the ugly hole to make it round so a plug can fit.  I'd be afraid to do that and am not sure how.   It seems like it would have to be a pretty big hole, and there isn't a whole lot of room there. 

BTW, my use of the word "ugly" was to distinguish between the two holes in the picture, not that I am worried about the aesthetics of it.  The only thing I am worried about is water intrusion.

Pro way of dealing with holes

https://youtu.be/kxWDhwfCgNE

There is a ton of excellent information on his channel.

Roland : I'd take a piece of tape and put it on the inside (underside) and the use glass or 5 minute epoxy to fill the hole.
For the hole in the stanchion itself, I'd take a screw and screw it in the hole with some butyl rubber!!

A few thoughts

On my boat, probably the most expensive, and totally squared-away, 1990 C34 in the world   I have a B&G Zeus electronics system and a Simrad hydraulic below deck autopilot. I like it all. Yes, the autopilot was a pain in the ass to install, requiring a custom glassed-in mount to support the ram and buying a new Edson tiller arm and drilling the rudder post to mount it. However, it all works well together, and fortunately, I was able to spend the dough to get good "boat worker" assistance to help me fumble through the job. I believe I posted some photos of the install last year. But if you are interested in more info email me.

Noah - I found this thread through CruisersForum, and am wondering if you could share more details on the plywood / fiberglass shelf you made for the mount? It looks like it extends upwards at least a foot, so there must be tremendous forces pushing against it - so it is impressive that it has held up. Is it 3/4" plywood and fiberglass? I see the buttress joints (not sure what to call these, but like an I-beam) which obviously add strength. But how is it attached securely to the hull floor? Can you recall how many layers of fiberglass and what weight? Thanks!

I am interested and could you pass along my email?   dfloeter99@yahoo.com.  thx

Just passing this along. Unsure if these can be adapted to y’alls, or maybe you know someone who can use them.... From 355 group:

4/24/19
Dear Group,
Has anyone bought or sold an asymmetrical sail and bow sprit recently?
I may have one, sparingly used for sale and I am trying to determine pricing.
 
Regards

https://groups.google.com/forum/m/?utm_medium=email&utm_source=footer#!msg/catalina355/ffuKMp-_02s/1_vtcXB2CQAJ

PT 728 is almost restored at the Liberty Aviation Museum in Port Clinton Ohio. Other WWII
 Restored artifacts . Also restoring a trimotor ford plus one that takes you for a flight over
The island. Always in the hanger is a B-25 and 3 or 4 times a summer a B-17  visits. Those
Flights are longer and more $$$,  but tours were free. Will be going to check out the
Progress on the PT  boat soon.  Check out the museum web site

As I mentioned above, I need to plug the hole in the deck.  Thanks Ken for your recommendation.