When I was corresponding with Marco about this, I remember we agreed how difficult it is to predict entropy behavior. There are just so many variables.
Take your example. Imagine a situation where "o" can be followed by a wide range of glyphs. Now, after your proposed transformation, it can only be followed by two glyphs. (Although now those two glyphs can be followed by everything that could originally follow "o", so you get a bunch of new combinations there).
So it's really hard to predict, but I would guess that in the majority of cases you'd be correct: splitting a glyph will normally increase the number of possible combinations and hence increase h2. I'll try to test this tomorrow, although I'm not sure yet how to replace half of all o's randomly. Humans are bad at random so it would have to be automated somehow. It would be the random (unconditional) selection that increases conditional entropy.
In a way, "splitting glyphs" is a method VM translators may use to add entropy back into the mix, for example by choosing whether to translate a glyph as "t" or "d". If this selection happens at the whim of the translator, it is not conditioned by surrounding glyphs so it will increase h2.
Edit: I must add that it is the same mechanism that eventually leads to one-way cipher solutions, because it would imply that a lot of information was lost upon incryption.
Take your example. Imagine a situation where "o" can be followed by a wide range of glyphs. Now, after your proposed transformation, it can only be followed by two glyphs. (Although now those two glyphs can be followed by everything that could originally follow "o", so you get a bunch of new combinations there).
So it's really hard to predict, but I would guess that in the majority of cases you'd be correct: splitting a glyph will normally increase the number of possible combinations and hence increase h2. I'll try to test this tomorrow, although I'm not sure yet how to replace half of all o's randomly. Humans are bad at random so it would have to be automated somehow. It would be the random (unconditional) selection that increases conditional entropy.
In a way, "splitting glyphs" is a method VM translators may use to add entropy back into the mix, for example by choosing whether to translate a glyph as "t" or "d". If this selection happens at the whim of the translator, it is not conditioned by surrounding glyphs so it will increase h2.
Edit: I must add that it is the same mechanism that eventually leads to one-way cipher solutions, because it would imply that a lot of information was lost upon incryption.