I$\newcommand\dotcup{\mathbin{\dot\cup}}$I shared your confusion until a year ago, when Markus Haase explained to me that (\eqref{2)} can actually be rewritten as assertion (ii) in the following theorem, which I find much clearer.
(i) The operator family $(T_i)_{i \in I}$ satisfies a maximal inequality, i.e., there is a constant $C \ge 0$ with the following property: for every $f \in E$ there exists $0 \le h \in L^p$ of norm $\|h\|_{L^p} \le C \|f\|_{E}$$\lVert h\rVert_{L^p} \le C \lVert f\rVert_{E}$ such that $|T_if| \le h$$\lvert T_if\rvert \le h$ for all $i \in I$ (where the inequality is to be understood pointwise almost everywhere).
(ii) There exists a constant $C$ with the following property: for every finite measurable partition $\Omega = A_1 \, \dot \cup \, \dots \, \dot \cup \, A_n$$\Omega = A_1 \dotcup \dotsb \dotcup A_n$, all indices $i_1, \dots, i_n \in I$$i_1, \dotsc, i_n \in I$, and every $f \in E$ one has $\Big\| \sum_{k=1}^n 1_{A_k} T_{i_k} f \Big\|_{L^p} \le C \|f\|_{E}$$\Bigl\lVert \sum_{k=1}^n 1_{A_k} T_{i_k} f \Bigr\rVert_{L^p} \le C \lVert f\rVert_{E}$.
For each $F \in \mathcal{F}$ the vector $0 \le \bigvee_{i \in F} |T_if| \in L^p$$0 \le \bigvee_{i \in F} \lvert T_if\rvert \in L^p$ (where $|\cdot|$$\lvert\cdot\rvert$ denotes the pointwise almost everywhere modulus and $\bigvee$ denotes the pointwise almost everywhere supremum) is norm bounded by $C\|f\|_{E}$$C\lVert f\rVert_{E}$. To see this, enumerate the elements of $F$ as $i_1, \dots, i_n$$i_1, \dotsc, i_n$ and choose a measurable partition of $\Omega$ into sets $A_1, \dots, A_n$$A_1, \dotsc, A_n$ such that $$ \bigvee_{i \in F} |T_if| = \sum_{k=1}^n 1_{A_k} |T_{i_k} f| = \Big| \sum_{k=1}^n 1_{A_k} T_{i_k} f \Big| . $$$$ \bigvee_{i \in F} \lvert T_if\rvert = \sum_{k=1}^n 1_{A_k} \lvert T_{i_k} f\rvert = \Bigl\lVert \sum_{k=1}^n 1_{A_k} T_{i_k} f \Bigr\rVert . $$ Since the net $\big(\bigvee_{i \in F} |T_if|\big)_{F \in \mathcal{F}}$$\bigl(\bigvee_{i \in F} |T_if|\bigr)_{F \in \mathcal{F}}$ in $L^p$ is increasing and norm bounded by $C\|f\|_{E}$$C\lVert f\rVert_{E}$, it is norm convergent to a vector $0 \le h \in L^p$ of norm $\le C\|f\|_{E}$$\le C\lVert f\rVert_{E}$ (here was used that $p \in [1,\infty)$). Clearly, $h$ satisfies the property claimed in (i). $\quad \square$
Remarks. (a) Assertion (i) is a convenient way to write down a maximal inequality if the index set $I$ is not assumed to be countable and if one does not make any regularity assumptions regarding the dependence of $T_i$ on $i$. Writing down the maximal operator before knowing whether a maximal inequality holds leads to measurability problems in this case. (But once the maximal inequality is established, one can define the maximal operator by using the supremum within the ordered space $L^p$ rather than the almost everyhwereeverywhere supremum.)
(b) In the situation of the question, assertion (ii) of the theorem is precisely the estimate (\eqref{2)} for simple functions $t: \mathbb{R}^n \to (0,1)$. So this shows, in particular, that it suffices to consider simple functions in (\eqref{2)}.
(e) Fun fact: The existence of $C$ is actually redundant in (i). Indeed, if one only assumes that for each $f \in E$ there exists $0 \le h \in L^p$ such that $|T_i f| \le h$$\lvert T_i f\rvert \le h$ for all $i \in I$, then there automatically exists a number $C \ge 0$ such that $h$ can always be chosen to satisfy $\|h\|_{L^p} \le C \|f\|_{E}$$\lVert h\rVert_{L^p} \le C \lVert f\rVert_{E}$. This can be shown by means of the closed graph theorem, see for instance (warning: shameless self-promotion ahead) Theorem 4.1 in the preprint this preprintOrder boundedness and order continuity properties of positive operator semigroups with Michael Kaplin.