Demo · no real money
You:

I want to back underdogs in LoL but only when the odds are really off

Teeny:

Then the entry should compare the market to the draft, not to the standings.

Buy the underdog when it is priced under 30¢ and has the stronger late-game composition. Hold through the mid game, and sell if the price reaches 50¢.

You:

how often does that happen?

Teeny:

Rarely: about one match in nine over the past month. The agent would be idle most days, which is the point of a rule this strict.