The "paradox" you are asking about is extremely interesting and I can only congratulate you on the dynamic way you are studyng mathematics.
1) The first confusing point is that for a holomorphic function $\phi$ on an open subset $U$ of a manifold, in your case $\phi_2$ and $U_2$ , the naïve notion of derivative \phi'(a) at a point $a\in U$ as a number does not work: you would get different numbers according to the chart you use.
The correct notion is that of a linear form on the tangent space $ d_a\phi:T_a (U) \to T_{\phi(a)} \mathbb R = \mathbb R $
The recipe for computing $d_a\phi$ is to choose a chart $w$ in a neighbourhood of $a$, to consider the composed function $\phi_w=\phi \circ w^{-1}$ and to decree that we have d_a\phi (t\cdot \frac {\partial}{\partial w}) =t\cdot \phi_w'(w(a)) \quad (t\in \mathbb R)
If you do that in your situation with $U=U_2, a=\infty, \phi=\phi_2=w$, you will find completely tautologically that $d_\infty (\phi_2):T_\infty (\mathbb P^1)\to \mathbb R $ is given by $d_a\phi_2 (t\cdot \frac {\partial}{\partial w})= t$, since $(\phi_2)_w=\phi_2 \circ w^{-1}$ is the identity.
2) The second confusing point is that you are not allowed to calculate $d_\infty\phi_2$ by means of the chart $\phi_1=z$ since its domain does not contain infinity: $\infty\notin U_1=dom(\phi_1)=\mathbb C$.
3) In the language of divisors (introduced on page 127 of your book) the divisor of the global meromorphic differential form $dw\in \Gamma ( \mathbb P^1, \Omega_X ^1 \otimes_{\mathcal O_X} \mathcal M_X)$ is $div(w)=-2\cdot (0)$ and for $dz\in \Gamma ( \mathbb P^1, \Omega_X ^1 \otimes_{\mathcal O_X} \mathcal M_X)$ it is $div(z)=-2\cdot (\infty)$.
Both results confirm that the line bundle of holomorphic $1$-forms on $\mathbb P^1$, a Riemann surface of genus $g=0$, has degree $2g-2=2\cdot0-2=-2$.