Ok, seems good.
Playing games also helps. If you get killed on the b1-h7 diagonal, you may not have named it but it's going to stick in your memory :p
What Diagonals were you killed on?
The ones that connect to knights often have attacking themes.
When I say "connect to knights" I means e.g. b1-h7-g8-a2
All diagonals are familiar to me for themes from different openings and maneuvers.
To some extent this is also why players can name the color of squares. They (or at least I) associate them with ideas and or pieces and or moves.
Interesting system, Ghost. The main problem I see with that system is that each of those summation numbers corresponds to two different diagonals. For example #6 could mean the "Vienna Diagonal" or "Bogo-Indian Diagonal". It wouldn't be hard to invent a prefix to specify which way the diagonal was running, as your "left" and "right" prefixes do, but another drawback is that those numbers aren't exactly intuitive.
LOWER LEFT TO UPPER RIGHT
(1) LIGHT
a8-a8 a8 1 #16
a6-c8 a6-b7-c8 3 #14
a4-e8 a4-b5-c6-d7-e8 5 "Spanish Diagonal" #12
a2-g8 a2-b3-c4-d5-e6-f7-g8 7 Italian Diagonal #10
b1-h7 b1-c2-d3-e4-f5-g6-h7 7 "Classic Diagonal" #8
d1-h5 d1-e2-f3-g4-h5 5 "Vienna Diagonal" #6
f1-h3 f1-g2-h3 3 #4
h1-h1 h1 1 #2
(2) DARK
a7-b8 a7-b8 2 #15
a5-d8 a5-b6-c7-d8 4 "Cambridge Diagonal" #13
a3-f8 a3-b4-c5-d6-e7-f8 6 #11
a1-h8 a1-b2-c3-d4-e5-f6-g7-h8 8 "Larsen Diagonal" #9
c1-h6 c1-d2-e3-f4-g5-h6 6 #7
e1-h4 e1-f2-g3-h4 4 "Fool's Mate Diagonal" #5
g1-h2 g1-h2 2 #3
UPPER LEFT TO LOWER RIGHT
(1) LIGHT
g8-h7 g8-h7 2 #15
e8-h5 e8-f7-g6-h5 4 "Scholar's Mate Diagonal" #13
c8-h3 c8-d7-e6-f5-g4-h3 6 #11
a8-h1 a8-b7-c6-d5-e4-f3-g2-h1 8 "Hungarian Diagonal" #9
a6-f1 a6-b5-c4-d3-e2-f1 6 #7
a4-d1 a4-b3-c2-d1 4 "Rubinstein Diagonal" #5
a2-b1 a2-b1 2 #3
(2) DARK
a1-a1 a1 1 #2
a3-c1 a3-b2-c1 3 #4
a5-e1 a5-b4-c3-d2-e1 5 "Bogo-Indian Diagonal" #6
a7-g1 a7-b6-c5-d4-e3-f2-g1 7 #8
b8-h2 b8-c7-d6-e5-f4-g3-h2 7 #10
d8-h4 d8-e7-f6-g5-h4 5 #12
f8-h6 f8-g7-h6 3 #14
h8-h8 h8 1 #16