When the tails come in pairs, you end with close to \$100. For example, with $n=7$, the following sequences of flips leave you with a large amount of money:
$$\begin{array}{rl}
TT\,TT\,TT\,H & $ 101\\
TT\,TT\,H\,TT & $ 101\\
TT\,TT\,H\,H\,H & $ 103\\
TT\,H\,TT\,TT & $ 101\\
TT\,H\,TT\,H\,H & $ 103\\
TT\,H\,H\,TT\,H & $ 103\\
TT\,H\,H\,H\,TT & $ 103\\
TT\,H\,H\,H\,H\,H & $ 105\\
H\,TT\,TT\,TT & $ 101\\
H\,TT\,TT\,H\,H & $ 103\\
H\,TT\,H\,TT\,H & $ 103\\
H\,TT\,H\,H\,TT & $ 103\\
H\,TT\,H\,H\,H\,H & $ 105\\
H\,H\,TT\,TT\,H & $ 103\\
H\,H\,TT\,H\,TT & $ 103\\
H\,H\,TT\,H\,H\,H & $ 105\\
H\,H\,H\,TT\,TT & $ 103\\
H\,H\,H\,TT\,H\,H & $ 105\\
H\,H\,H\,H\,TT\,H & $ 105\\
H\,H\,H\,H\,H\,TT & $ 105\\
H\,H\,H\,H\,H\,H\,H & $ 107\\
\end{array}
$$
There are $F(n+1)$ such “good” sequences of flips, where $F(n)$ is the $n$th fibonacci number, approximately $\frac1{\sqrt 5}\phi^n$ where $\phi\approx 1.618$. For large $n$, this is an insignificant fraction of the space of all flips. But when $n$ is small, say $n=7$, then it is significant. For $n=7$ there are $F(7+1) = 21$ such “good” sequences of flips out of 128. So we can get a very rough estimate that the expected result for $n=7$ is around $$\$100\cdot \frac{21}{128} + \$1\cdot \frac{115}{128} \approx \$17.24$$ which is not too far off from what the computer simulation says.
To get a better estimate, we need to account for the fact that the big winning jackpots exceed \$100 by up to $n$ dollars each, and that when all the tails appear in pairs, plus there is one more tail at the end, (as $H\,TT\,H\,TT\,T$ for example) then we end not with close to \$1 but with close to \$0.
When $n$ becomes large, $2^{-n}F(n+1)\ll1$, because $\phi<2$, so the additional contribution of the lucky flips (and the unlucky flips) becomes insignificant, and the expected return is close to $1$.