Thoughts...
Dear Mike,
In order of appearance:
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Curious to know if anyone has:
1. Found a way to separate the left and right ditch lights with Decoder Pro?
Per your provided pic, "separating the Ditch Lights" is a Hardware (wiring) issue,
not a "can tweak by CV" Software issue. Pass the soldering iron... 
Hint: a key clue is the number of wires feeding the daughterboard.
I wonder where a Digital Multimeter would say Points 2 and 4 trace to?
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2. Assuming 1 is infeasible, had one of these apart and tackled rewiring the ditch lights
Given your previous experience, I would have thought this should be a doddle.
Pass the 0603 SMD LEDs and Resistors, piece of Clover House PCB tie, solder and soldering iron... 
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3. Figured out how to program a L-L-S-L Grade Crossing Horn Song on an ESU, and map it to a Function to trigger the ditch lights.
Short answer : No
Slightly-Longer answer : If you're specifically looking for a "RTR canned ST-style" grade crossing horn-blow, No
Complete answer : Yes, this is entirely possible with an ESU LokSound decoder.
You will need:
Ingredients
- a Suitable Decoder
- a copy of the existing Bowser Sound Project or equivalent
- a LokProgrammer HW + SW rig
- a suitable sound file (WAV) with the exact "Grade crossing horn blow sequence" you desire
Recipe:
- Connect your Host PC, LokProgrammer, and subject decoder together
- Launch the LP software, and open the Donor (Bowser?) project
- Import your desired "Horn blow sequence" WAV audio file
- Assign the WAV file to a SoundSlot
(You may either replace a redundant sound is an existing SoundSlot,
or use a free SoundSlot to Add the file to the Project without loosing any Existing sounds,
assuming the Decoder has the Storage to handle the additional sound file)
- Using the "Function Mapping" (aka "Mapping Rows" in LokProgrammer parlance)
Map a given "F-key" INPUT to Trigger the relevant SoundSlot
(this will be your "blow the Grade Crossing sequence" F-key)
- Using the "Function Mapping" (aka "Mapping Rows" in LokProgrammer parlance),
Map the Function to trigger the "Grade Crossing Logic" Logical Function
Result
- The Ditch Lights are turned ON/OFF by a given "F-key"
- Pressing the "Grade Crossing Horn Sequence" F-key (as configured above) triggers the custom "Grade Crossing Sound" sound-file you loaded, AND triggers the "Grade Crossing Mode"
- "Grade Crossing Mode" provokes the Ditchlights to flash
- and they continue to flash until the configured "Holdover time" expires
(at which point the Ditchlights will revert to either "constant ON" or "constant OFF",
depending of whether you are using "Ditch Light Mode #1" or "Ditch Light Mode #2" respectively)
NB that Manually blowing L-L-S-L should also trigger the "Grade Crossing Logic" and thus flash the ditch-lights,
every "trigger" of the Horn will reset the "Hold-over timer", so the last-blast --> ditch-lights-stop-flashing time is deterministic/consistent.
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4. Figured out how to get the headlights to dim. I've tried every setting I could find. No joy.
In order of diagnostic:
- What Lighting Mode is the Front and Rear Headlights?
(should be either "1. Dimmable Light" or "2. Dimmable Light (Fade In/Out)"
See Page 79 and 82 of the LokSound 5 Manual)
- What "Brightness Value" is the Front and Rear Headlights set for?
(should be between 0 and 31,
See Page 79 and 82 of the LokSound 5 Manual)
HINTS:
CV31 = 16, CV32 = 0
CV259, 262 and 263 are currently What Values?
CV267, 270, and 271 are currently What Values?
I hope this helps...
Happy Modelling,
Aim to Improve,
Prof Klyzlr