Highest Possible Crit Range?

[ocdscale]

isn't that called the gambler's fallacy?

You might be thinking of two things.
Gambler's fallacy is that things "even out" over time. When someone thinks: If a fair coin lands heads four times in a row, it's more likely to land on tail's this time.

Gambler's ruin is a little more relevant, but does not apply because the proposed build is weighted towards successes instead of being 50/50.
Or the other version of Gambler's ruin (one that incorporates preferential odds) is not applicable because your wager is not a fixed percentage of your bankroll. Your wager is fixed to 1 attack, while your bankroll (number of attacks) grows.
*terminally sick has read a proof that has convinced him that even preferential weighting will not escape Gambler's ruin. I haven't seen the proof, but I disagree (although I trust judgment enough to worry about it).