Well, you can make numbers from 1 to 110, that's 110 possible states you can be in. That's a large transition matrix, but not intractable. Define transition matrix $M$ as:
$$\begin{align}
M_{i,j} = \begin{cases}
\frac{1}{10} & \text{ if } 1 \le j - i \le 10 \text{ and } 1 \le i \le 100 \\
1 & \text{ if } i = j\text{ and } 100 < i \le 110 \\
0 & \text{ otherwise}
\end{cases}
\end{align}$$
Define the initial state vector:
$$\begin{align}
V_{j} = \begin{cases}
\frac{1}{10} & \text{ if } 1 \le j \le 10 \\
0 & \text{ otherwise}
\end{cases}
\end{align}$$
This matrix compute the probability that you end up in state $j$. I won't wrote out the whole thing here. The steady state $S$ is given by:
$$S = VM^{\infty}$$
I don't recommend doing this by hand.
Anyway, you get the following probabilities:
$$\begin{array} {c|c}
\text{End State} & \text{Probability} \\ \hline
101 & \frac{{
14545454540916238222253308031039403263876427137099 \atop
728738149747953197899302063661139633020606426446001
}}{10^{101}} \\ \hline
102 & \frac{{
18181818143103207886299794518678653455112915813572 \atop
471568730433172695421560362344285718841548526446001
}}{10^{101}} \\ \hline
103 & \frac{{
16363636337149401877562367260240328253764897737948 \atop
745622241485421850822156839220501392260147526446001
}}{10^{101}} \\ \hline
104 & \frac{{
12727272741576429962125352735631301525861758140731 \atop
984148880861015973102098820410322797857111216446001
}}{10^{101}} \\ \hline
105 & \frac{{
10909090931874858870242133363925460156752233410373 \atop
601637391699278967219484863685353489177266485446001
}}{10^{101}} \\ \hline
106 & \frac{{
90909091116377120481295620461022602720063194921283 \atop
52571281564919296780386873223909380629437281346001
}}{10^{101}} \\ \hline
107 & \frac{{
72727272852713068490158133017227152668140086810036 \atop
91839439446721479480174650845945205326825156836001
}}{10^{101}} \\ \hline
108 & \frac{{
54545454582842347527531906998645390126303113111522 \atop
24370063982379262253640845972771391003951819875001
}}{10^{101}} \\ \hline
109 & \frac{{
36363636346255163502142715869656509893927302281916 \atop
05910755643757924951410231819125651609791149217901
}}{10^{101}} \\ \hline
110 & \frac{{
18181818155610931814042064558296878037883980477975 \atop
93593065135379352069784448816645340273314411495091
}}{10^{101}} \\ \hline
\end{array}$$
Expected state is calculated as always, and the final answer is :
$$\sum_{k=100}^{109} k\cdot S_{j,k} = \frac{{
2080000000053214123545556126144601328836935442611255 \atop
847240374822309959920561393884518831211143790906011
}}{2\cdot10^{100}}$$
which is almost exactly $104$ (to eight decimal places).
EDIT-- Corrected post, originally answered the question "at least 100" rather than "more than 100".
The expected value of a sum of random number $N$ of iid random variables $X_i$ is
$$E\left[\sum_{i=1}^N X_i\right]=E[N]E[X_i]$$
In your case you add $E[N]$, so the answer is
$$E[N]E[X_i]+E[N]=3.5\cdot 3.5+3.5 =4.5\cdot 3.5 = 15.75$$
Best Answer
Solution 1: We roll the die and add the value. With $5/6$ probability we start again. Hence,
$$E(X) = \frac{7}{2} + \frac{5}{6}E(X)$$
and this gives $E(X) = \boxed{21}$.
$E(X) = \infty$ is also a solution, so we should show that the expectation is finite. This is equivalent to showing that the expected number of rolls is finite, since the expected value is bounded between the number of rolls and six times the number of rolls. By standard methods, the expected number of rolls is
$$\sum_{n=0}^{\infty} (n+1) \frac{1}{6} \left(\frac{5}{6}\right)^n$$
which converges to $6$. We can use this to motivate a secondary method:
Solution 2: On average we roll $6$ times. The average on a roll is $\frac{7}{2}$. Hence the answer is $21$.
You might ask, but doesn't it matter that we can't roll a six or else we stop? Each roll still has the same expectation of $\frac{7}{2}$, it is just that we stop arbitrarily when we happen to roll a six.
(This perhaps unintuitive logic is similar to that in the problem involving a town where couples birth babies until their first boy and then stop. The proportion of boys to girls in this town is still $1:1$ since each birth is still just an independent event; they just choose to stop arbitrarily when the first boy comes)