Thanks everyone for the input, to the person it was all spot on. To provide some closure on this thread:
Thought about removing the entire stern rail but decided to exhaust other options before taking that on. The boat is on a mooring and we're actively sailing her as much as possible.
The SS plate turned out to be solid across it's footprint and ~3/16" in thickness. Even though access was very restricted, finding center was easy as I could see the 3 through bolts from underneath. Using fresh bits and cutting paste, I was able to get a 1/8" pilot bit up through the plate after first drilling through the glass, core and gelcoat (happy to see that the core was in excellent condition). The drilled glass and core worked well as a guide path to hold the bit so it didn't wander when the initial pilot hole was tapped through the SS plate. After that, I just increased the bit size in 6 increments from 1/8" to 3/8", vacuuming it out after each pass. Using a variable speed drill, I kept the speed as low as practical. Per Maine Sail's tutorial, I removed ~1/4" of surrounding core in the newly hollowed out hole. I used a dremel and micro router bit. It's been over filled with neat and then slightly thickened epoxy from below using a syringe and tape. Will re-drill tomorrow then countersink the epoxy from below and fish the wire. Before filling with epoxy, I did a test run on fishing the wire from below decks, pushing the wire up through the stern rail. I'm sure this will jinx the final install, but I was surprised how easily the wire traveled up through the tube, around the bend above decks and up to the hole I made in the horizontal rail. Nothing ever goes that smoothly when working on a boat.
As an aside, to drill the hole in the horizontal stern rail tubing above decks I used a tip posted somewhere on the net. Using a dremel and cutoff disc, I scored two short and shallow perpendicular cuts to form a "+" in the SS. The pilot drill bit into that immediately without wandering at all. Not my idea, but a very cool trick for drilling into tubular steel.
All of this effort is to install a small 30W solar panel to maintain the battery while on a mooring. To FastOlson's point, 3 weeks into this project and 95% of the time has been spent researching, planning, modeling the panel brackets, ordering supplies and prepping the boat. All for a few watts of power a day... but that's for a separate post.
Thanks again everyone