Old dryer vent in concrete

It will work as well as the previous path has. Building the slope into the path means you don't have to worry so much about the base - one of the main reasons for a good crushed rock base is to aid in draining. Also, this is not a large slab area - it's just a narrow path, so going with a packed dirt/clay base is fine.

In the worst case, you'll shovel it back into a mesh to separate the pebbles from the dirt, and re-lay it out later, but I expect if you follow the design of the existing path you'll be just fine. It'll match better as well.

Hopefully those holes are actually sloped upward the entire way, but I would not count on it.

Silicon would be OK, especially deep in. But there's a product called Mor-Flexx which is specifically made to look and work like mortar. A tube of this would work better than any mastic, as you can really squirt it far in. Plus you can touch up any other cracked masonry you might have around the house.

I might also solve this exact problem using rapidset mortar in a pastry bag (to get the mortar deep into the brick). But this can crack brick over the decades if the mortar is harder than the brick and thus expands differently (a problem in historic renovation, as older bricks are often softer than modern mortar).

That said, the Mor-Flexx is easy and will solve the problem completely. You can then install a weatherproof cable entry point and all future installers will take the lazy way out and use it (who wants to drill brick if you don't have to?).