what we're doing now is a combination of skew as mean reversion and skew as a directional assumption.. we're definitely heavily focused on maximizing number of occurrences as well.. as for the intricacies, i've definitely been flying thru those...ergodicity and non-ergodicity, fat tail distributions, and all the other little intricate correlations and considerations most people who discover skew trading never think to even look at..
the part about kelly, that's just about making sure i'm understanding the position sizing aspect correctly.. the intricacies of probabilities-based trading is a whole different topic.. in my experience tho, i must say, i've been able to do exceedingly well trading skew.. i did take some big losses in this recent downturn as there were some factors i wasn't considering prior (i.e., increased tail risk/risk of ruin, probability of max loss vs probability of max reward independent of net expected value, absorption risk, modulating the shape of your portfolio's volatility curve against the assets you're trading, etc.).. but overall the strategy has been immensely successful..
i also trade a lot lol.. i think i've done over 1,000 trades this year alone? as you said, you need a high number of occurrences..