Let $A_{m,n}$ be the probability that player $A$ flips two consecutive heads before player $B$ flips three consecutive heads, given that $A$'s (resp. $B$'s) current run of heads has length $m$ (resp. $n$). Then
$$
A_{m,n}=\frac{1}{4}\left(A_{m+1,n+1} + A_{m+1,0} + A_{0,n+1}+A_{0,0}\right);
$$
the boundary conditions are that $A_{m,n}=1$ for $m\ge 2$ and $n < 3$, and $A_{m,n}=0$ for $m \le 2$ and $n\ge 3$. You want to find $A_{0,0}$. The relevant six equations are:
$$
\begin{eqnarray}
A_{0,0} &=& \frac{1}{4}A_{1,1} + \frac{1}{4}A_{1,0} + \frac{1}{4}A_{0,1} + \frac{1}{4}A_{0,0}\\
A_{0,1} &=& \frac{1}{4}A_{1,2} + \frac{1}{4}A_{1,0} + \frac{1}{4}A_{0,2} + \frac{1}{4}A_{0,0} \\
A_{1,0} &=& \frac{1}{2} + \frac{1}{4}A_{0,1} + \frac{1}{4}A_{0,0} \\
A_{1,1} &=& \frac{1}{2} + \frac{1}{4}A_{0,2} + \frac{1}{4}A_{0,0} \\
A_{0,2} &=& \frac{1}{4}A_{1,0} + \frac{1}{4}A_{0,0} \\
A_{1,2} &=& \frac{1}{4} + \frac{1}{4}A_{0,0},
\end{eqnarray}
$$
or
$$
\left(\begin{matrix}3/4 & -1/4 & -1/4 & -1/4 & 0 & 0 \\
-1/4 & 1 & -1/4 & 0 & -1/4 & -1/4 \\
-1/4 & -1/4 & 1 & 0 & 0 & 0 \\
-1/4 & 0 & 0 & 1 & -1/4 & 0 \\
-1/4 & 0 & -1/4 & 0 & 1 & 0 \\
-1/4 & 0 & 0 & 0 & 0 & 1
\end{matrix}\right)\times\left(\begin{matrix} A_{0,0} \\ A_{0,1} \\ A_{1,0} \\ A_{1,1} \\ A_{0,2} \\ A_{1,2}
\end{matrix}\right)
= \left(\begin{matrix}
0 \\
0 \\
1/2 \\
1/2 \\
0 \\
1/4
\end{matrix}\right),
$$
assuming no typos. Further assuming no typos entering this into WolframAlpha, the result is
$$
A_{0,0} = \frac{1257}{1699} \approx 0.7398,
$$
which at least looks reasonable.
Update: As pointed out in a comment, the above calculation finds the probability that $A$ gets two consecutive heads sooner than $B$ gets three consecutive heads; the original problem asks for the opposite. The correct boundary conditions for the original problem are that $A_{m,n}=1$ for $m<2$ and $n\ge 3$ and $A_{m,n}=0$ for $m\ge 2$ and $n\le 3$. The matrix equation becomes
$$
\left(\begin{matrix}3/4 & -1/4 & -1/4 & -1/4 & 0 & 0 \\
-1/4 & 1 & -1/4 & 0 & -1/4 & -1/4 \\
-1/4 & -1/4 & 1 & 0 & 0 & 0 \\
-1/4 & 0 & 0 & 1 & -1/4 & 0 \\
-1/4 & 0 & -1/4 & 0 & 1 & 0 \\
-1/4 & 0 & 0 & 0 & 0 & 1
\end{matrix}\right)\times\left(\begin{matrix} A_{0,0} \\ A_{0,1} \\ A_{1,0} \\ A_{1,1} \\ A_{0,2} \\ A_{1,2}
\end{matrix}\right)
= \left(\begin{matrix}
0 \\
0 \\
0 \\
0 \\
1/2 \\
1/4
\end{matrix}\right),
$$
The result becomes $A_{0,0}=\frac{361}{1699}\approx 0.2125$. The two results add to slightly less than one because there is a nonzero probability that both players hit their goals at the same time... this probability is $81/1699\approx 0.0477$.
I ask you for additional explanation. Meanwhile I'll post here another approach.
Denote by $\tau_i^5$ the random variable that counts the time required to get five heads starting from $i$ heads, ok?
What we want is exactly $E[\tau_0^5]$, right?
Now, you can evaluate $E[\tau_0^5]$ conditioning at the first step.
$$
E[\tau_0^5] = \frac{E[\tau_0^5]}{2} + \frac{E[\tau_1^5]}{2} +1
$$
Explaining the equation above. With probability $1/2$ you have a tail, so the time you will take to get five heads is the same, because you have any heads. On the other hand, with the same probability you get a head, and now, the number of flips needed to get 5 heads is $E[\tau_1^5]$, because now you that you have one head. The +1 it is because you have to count the first step.
Repeating the argument above you get
$$
E[\tau_1^5] = \frac{E[\tau_0^5]}{2} + \frac{E[\tau_2^5]}{2} +1
$$
Proceeding this way, and remembering $E[\tau_5^5]=0$, you get
$$
E[\tau_0^5] = 62
$$
This may seems more complicated at the first sight, but the idea of "to conditionate at what happens at the first time (or movement)" solve a big variety of problems.
Best Answer
Once you have got 3 consecutive heads, your goal is attained, and the task is over.
1.The probabilities in question obtained after N trials are the cumulative probabilities.
2. No, you can't say that. $P(N \le 8)$ is the probability that at most $8$ flips are needed.
you can understand from the probability values for trials 3 through 8
$3\quad 0.125 000 000$
$4\quad 0.187 500 000$
$5\quad 0.250 000 000$
$6\quad 0.312 500 000$
$7\quad 0.367 187 500$
$8\quad 0.417 968 750$