This is not aimed at any particular engine or programmer, but an open-ended discussion that others should chime into with further on-topic comments or observations.
Firstly, I'd like to start off with a basic diagram illustrating a pointy chain that's directed at the enemy Kingside. (By the last statement, I mean that the Black King is situated on the short side of the board relative to the White pawn chain, namely on the g or h file) Let's not assume that these are the only pieces present on the board - indeed, if that were the case, there would hardly be any advantage conferred by the pointy chain.
[d]6k1/6pp/5p2/4pP2/3pP3/3P2P1/7P/6K1 b - - 0 1
The above position was arrived at after White's f4-f5, thus favorably 'extending the pawn chain'. Assuming sufficient material is on the board (i.e. especially the Queen and a bunch of other pieces - but more on this later), it is my contention that the d3-e4-f5 White chain is not only superior to the (longer) Black chain (g7-f6-e5-d4), but actually should give White a clear advantage due to far better Kingside attacking chances. The same considerations would hold true if the position was horizontally mirrored, and Black had the pointy chain directed at the White Kingside, as in the King's Indian proper. Also, I should quickly mention that the offensive pointy chain should contain at least 3 chain pawns, since a 2-pawn chain is much easier to undermine and would confuse the issue.
There's one more essential element present in the set-up in the above diagram that helps tip the balance in favor of the pointy chain directed at the Kingside, which I have not mentioned yet. [Without this element, the the position would likely be up for grabs, and the correct evaluation would probably depend on a myriad of other factors, rendering the whole pointy chain idea far less effective.] I invite the reader to take a good look at the position and try to determine what it might be.

OK, let's now compare the previous diagram with this one:
[d]6k1/6pp/5p2/2p2P2/3pP3/3P2P1/7P/6K1 b - - 0 1
We still have a pointy chain aimed at the Kingside, following the f4-f5 advance, but something is seriously amiss. There is no longer a black pawn on e5, and this should throw White's set-up for a loop. Again, it's my contention that that the pointy chain is no longer so favorable, as Black can use the open square on e5 in a number of ways to come up with effective counterplay.
So, it seems that our pointy chain concept really hinges on the presence of this pawn on e5. Here I would like to define a new term to aid us in our understanding - I'd like to call such a pawn as the one on e5 a congestion point, and it can be a favorable or unfavorable feature of the position depending on which way the chains are pointing, relative to the opposing Kingside.
While at it, let's come up with a better term for the foremost pawn at the tip of our pointy chain - I'd like to call it the spearhead. This will help us to better define the congestion point as the pawn directly in front of the chain pawn that is defending the spearhead. Its presence next to the spearhead is essential to the effectiveness of pointy chains in general, as it helps create a barrier that both hinders the defender and aids the attacker.
I suspect that prior attempted implementations of the pointy chain may have ignored the presence or absence of a congestion point pawn, and therefore failed as a result. Another point of failure may involve incorrectly defining the opposing King's danger zone relative to the pointy chain, but more on this later.
In part 2, later on, I'd like to go over pointy chains directed at the Queenside, and further elaborate on congestion points.
(End of part 1 here)
Regards,
CL