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First 'proof of concept'

First Serial Data Shown

early non-inversed output

Output pin enabled 1 cycle too late

Output pin correctly enabled

Self Documenting Hardware!
Dithered characters (176, 177 and 178) don't tile particularly well on an (8+1)x9 pixel grid. I've attempted to reduce the effect by having a more 'granular' pattern, but it's not perfect.