Working out EV is easy for casino table games, relatively easy for poker and extremely difficult for stocks trading.
“The market can remain irrational longer than you can remain solvent.”
Technically, EV has nothing to do with sample size. But I get your point that in sufficiently small sample sizes and/or sufficiently large bet sizes you might need to think about utility rather than expectation.
I don't believe EV is easier to estimate in poker than trading. You need to estimate hand range and the consequences of actions later in the hand. It's extremely complicated.
Looking at the closing price for each trading day, count how many times the stock ended higher and how many times it ended lower than the previous day.
Then you have your odds.