Ok, here goes.
The number of tails you flip before the first head is unimportant. So we can ignore them and assume the first flip gives us a head.
When N=2, the chance of winning outright is 1/2, and the chance you will go to N=3 is also 1/2.
When N=3, the chance of winning is 1/4, there is a 1/2 chance of going to N=4, and a 1/4 chance of gooing to N=5.
When N=4:
1/8 Win
1/2 go to N=5
1/4 go to N=6
1/8 go to N=7
And so on.
What we want to do is add up all the probabilies of wins. The terms of this seris will be the probability of an outright win for a given N times the probability of ever getting to that N.
1/2 * 1 + 1/4 * 1/2 + 1/8 * 1/2 * 1/2 + 1/16 * 1/2 * 1/2 * 1/2 + 1/16 * 1/4 * 1/2 …
This last term is where things get interesting.
The last two terms both represent N=5. One term is the chance of winning N=5 when you were last at N=4, and the other is winning N=5 when you jumped from N=3 straight to N=5.
There are two ways to get to N=5 and N=6.
There are three ways to get to N=7 and N=8.
4 ways to 9 and 10 and so on…
However, we can just carefully order our terms like so to get the answer…
1/2 +
1/4 * 1/2 + 1/8 * 1/2 * 1/2 + 1/16 * 1/2 * 1/2 * 1/2 + 1/32 * 1/2 * 1/2 * 1/2 * 1/2 … + (this represents the probability of winning after being at N-1)
1/16 * 1/4 * 1/2 + 1/32 * 1/4 * 1/2 * 1/2 + 1/64 * 1/4 * 1/2 * 1/2 * 1/2 … + (this represents the probability of winning after being at N-2)
1/64 * 1/8 * 1/2 * 1/2 + 1/128 * 1/8 * 1/2 * 1/2 +1/2 …+ (this represents the probability of winning after being at N-3)
…and so on. The important thing to note is that each of these longer lines is a geometric series which has a sum that we can compute.
That gives us…
1/2 +
1/8*(1 + 1/4 + 1/16 + 1/64…) +
1/128*(1 + 1/4 + 1/16 + 1/64…) +
1/2048*(1 + 1/4 + 1/16 + 1/64…) + …
The sum of the geometric series in parenthesis is 1/(1-1/4) or 4/3
Substitute this in and we get
1/2 +
1/8 * 4/3 + 1/128 * 4/3 + 1/2048 * 4/3 + …
This is also a geometric series. We can rewrite it as:
1/2 + 1/6*(1 + 1/16 + 1/256 + …)
The sum of the geometric series in parenthesis is 1/(1-1/16) or 16/15.
When we substitute this in we get.
1/2 + 1/6*(16/15) = 61/90
This is the exact answer.