Since every rational has a cyclic fractional part, let's explicit Momo's answer with full sum notation. It is a little tedious, and shows why the overline notation is so powerful, but anyway, let's do it!
$\frac{1}{7}=0.[142857]...=\sum\limits_{k=1}^{\infty}142857\times10^{-6k}$
$$\frac{1}{7}=\sum\limits_{k=1}^{\infty}c_{k-1}\,10^{-k}$$
With $c_0=1,\;c_1=4,\;c_2=2,\;c_3=8,\;c_4=5,\;c_5=7$
$c_{6q+r}=c_{r}$ for $r=0\,..\,5$
REM: I change a little bit $a_i$ definition to ease expressions
$$a_{i}=\lfloor\frac{10^{2+i}}{7}\rfloor-100\lfloor\frac{10^i}{7}\rfloor$$
Let's have a look at
$$a_i=\lfloor\sum\limits_{k=1}^{\infty}c_{k-1}10^{2+i-k}\rfloor-100\lfloor\sum\limits_{k=1}^{\infty}c_{k-1}10^{i-k}\rfloor$$
Let's note partial sums $S(k_0,k_1)=\lfloor\sum\limits_{k=k_0}^{k_1}c_{k-1}10^{2+i-k}\rfloor-100\lfloor\sum\limits_{k=k_0}^{k_1}c_{k-1}10^{i-k}\rfloor$
$a_i=S(1,\infty)=S(1,i)+S(i+1,i+2)+S(i+3,\infty)$
We notice that in $S(1,i)$ since $k\le i$ the powers of $10$ are positive so we can get rid of the floor function, these all are integers.
$S(1,i)=\sum\limits_{k=1}^{i}c_{k-1}\,10^{2+i-k}-100\sum\limits_{k=1}^{i}c_{k-1}\,10^{i-k}=0$ since both terms are equal.
We notice that $k\ge i+3$ then $(i-k)<0$ and $(2+i-k)<0$.
All powers of $10$ are strictly negative, thus the sum is $<1$ and floor value is $0$.
$S(i+3,\infty)=0-100\times 0=0$
It remains only one term :
$S(i+1,i+2)=\lfloor c_{i}10^1+c_{i+1}10^0\rfloor-100\lfloor c_{i}10^{-1}+c_{i+1}10^{-2}\rfloor$
The first term is an integer, and the second one is $<1$ thus
$S(i+1,i+2)=c_{i}10^1+c_{i+1}10^0-100\times 0=10c_{i}+c_{i+1}$
$$a_i=10\,c_i+c_{i+1}$$
So since the $c_i$ are cyclic, the values for $\{a_i\}_i$ are $\{14,42,28,85,57,71\}$ and the max is $85$.