I wrote a Maple program in 2003 which computes $P(\alpha)$ (both the "upper" and "lower" values) for a given rational number $\alpha$, much in line with the method described by Johan. I think I was able to compute it for all $\alpha=a/b$ for integers $1\le a\lt b\le 300$ in a couple of hours, so the program could probably compute fairly good approximations to $P(1-2/\log_2(p))$ when $p$ is not too large. (Edit: When $p$ is large, $1/2$ will be a very good approximation. For example, if $p\gt1000$ then $0.499\lt P(1-2/\log_2(p))\lt1/2$.)
I didn't publish any of this, but much of it is contained in the article "The Maximum Average Gain in a Sequence of Bernoulli Games" by Wolfgang Stadje (American Mathematical Monthly, December 2008).
EDIT: Since I don't have access to Maple anymore, I translated the program to Matlab:
function p=p(s,t);
d=gcd(s+t,2*t);
s=(s+t)/d;
t=2*t/d;
pol=zeros(1,t+1);
pol([1 s+1 t+1])=[1 -2 1];
r=roots(pol);
[rsort,i]=sort(abs(r));
p=1-prod(abs(1-r(i(1:t-s))));
The program computes $P(s/t)$ for integers $0\lt s\lt t$, by computing $1$ minus the product of $1-r$ for those zeroes $r$ of $z^{2t/d}-2z^{(t-s)/d}+1$ that have absolute value less than $1$ (there are $(t-s)/d$ of them), where $d=\gcd(s+t,2t)$.
By the way, in my notes I found the lower bound $P(\alpha)\ge A$, where $\alpha=1-\frac{2\log A}{\log(2A-1)}$, with equality for $\alpha=(k-2)/k$. I think Johan was involved in obtaining this bound.
EDIT (May 14): So, here is a fairly detailed proof of the formula used in the program above.
Lemma 1. For integers $0\lt 2b\lt a$, the polynomial $g(z)=z^a-2z^b+1$ has no multiple zeros and exactly $b$ zeroes inside the unit circle.
Proof. If $g(z)=g'(z)=0$ then $z\ne 0$ and
$$0=g'(z)=az^{a-1}-2bz^{b-1}=z^{b-1}(az^{a-b}-2b),$$
so $az^{a-b}-2b=0$. Hence, $0=g(z)-g'(z)*z/a=1-2(1-b/a)z^b$ so that $|z|^b=\frac1{2(1-b/a)}=\frac a{2(a-b)}$. Also, $az^{a-b}-2b=0$ so $|z|^{a-b}=2b/a$. This implies that
$$\left(\frac a{2(a-b)}\right)^{a-b}=\left(\frac{2b}a\right)^b.$$
This can be rewritten as $2(1-b/a)^{1-b/a}(b/a)^{b/a}=1$. But it is easily checked that $2(1-y)^{1-y}y^y\gt1$ for $0\lt y\lt1/2$, a contradiction.
The second part can be proved by a straight forward application of Rouché's theorem.
Lemma 2. Suppose that $\sum_{i=1}^kA_ir_i^{-j}=1$ for $1\le j\le k$. Then $\sum_{i=1}^kA_i=1-\prod_{i=1}^k(1-r_i)$.
Proof. The equations can be seen as a system of linear equations in $A_1,\dots,A_k$, and the result can be obtained by using Cramer's rule and Vandermonde determinants. I skip the details. (Actually, I think I had a simpler proof of this lemma, but I could neither find it in my notes, nor figure it out right now.)
Now, let $L=\max_{n\gt0}{S_n/n}$, so that $P(\alpha)=P(L\gt\alpha)$. Also, let $Y_i=(X_i+1)/2$ and $T_n=\sum_{i=1}^nY_i$ (so that $T_n$ is a random walk with steps $0$ and $1$ instead of $\pm 1$). (The main reason for this is that my original result was for $T_n$, but I also think that the formulae get a little simpler in this case.)
Let me restate the result I am going to prove:
Theorem. For integers $0\lt s\lt t$, $P(s/t)=1-\prod_{i=1}^{t-s}(1-r_i)$, where $r_1,\dots,r_{t-s}$ are the zeroes of $z^{2t}-2z^{(t-s)}+1$ that have absolute value less than $1$.
Proof. Let $M=\max_{n\gt0}{T_n/n}$ and $Q(\alpha)=P(M\gt\alpha)$. I will prove the corresponding result for $Q(s/t)$, and then translate it to $P$, using the fact that $T_n=(S_n+n)/2$ which implies that $P(\alpha)=Q((\alpha+1)/2)$.
Suppose then that $1/2\lt s/t\lt1$ and consider $Q(s/t)$. Just as Johan did, we define another random walk $U_n=\sum_{i=1}^nZ_i$ with steps $Z_i=s$ or $Z_i=s-t$ so that $Q(s/t)$ equals the probability that $U_n$ will ever reach $-1$, define $f(j)$ as the probablity that $U_n$ will reach $-1$ when it is currently at $j$, and find that $f(j)=f(j+s)/2+f(j+s-t)/2$ for $j\ge0$. The characteristic equation of this recursion is $g(z)=z^t-2z^{t-s}+1=0$. By Lemma 1 and since $f(j)$ tends to $0$ as $j$ tends to infinity, we must have $f(j)=\sum_{i=1}^{t-s}A_ir_i^j$, where $r_1,\dots,r_{t-s}$ are the (necessarily simple) zeroes of $g(z)$ inside the unit circle. Since $f(j)=0$ for $s-t\le j\le -1$, Lemma 2 implies that $Q(s/t)=f(0)=\sum_{i=1}^{t-s}A_i=1-\prod_{i=1}^{t-s}(1-r_i)$.
Now, if $0\lt s/t\lt1$ then $P(s/t)=Q((s+t)/(2t))$, which, by what we have just proved, equals $1-\prod_{i=1}^{t-s}(1-r_i)$, where $r_1,\dots,r_{t-s}$ are the zeroes of $z^{2t}-2z^{t-s}+1$ inside the unit circle. This concludes the proof.