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The basic reason is that the cocycle you mentioned, integrating from $i$ to $\gamma\cdot i$, vanishes on $S$, which means it can't be nonzero for a cuspidal cycle, which vanishes on the other generator $T$.
Shimura has written several books. There were at least five in our library and a cursory glance did not reveal anything to do with cocycles or cohomology. I agree that taking any $z$ in the upper half plane and integrating $z$ to $\gamma z$ will give a cocycle for any modular form, but you can't get enough of them this way. To get most of them, you have to start with a point on the boundary, such as $0$, but this construction only seems to be well-defined for cuspidal forms.
I know that for cuspidal forms $f(z)$ you integrate $f(z)z^s$ from $0$ to $\gamma 0$ to get a cocycle. I guess you're saying I should do a similar thing, but not use a boundary point.