At least for games, I check how big is the dev team, anything bigger than 30 then pirate Then I check if owner of the development studio is public company, if yes then pirate Then I check if owner owns more than one development studio, if yes then pirate Then I check how many games studio has released, if more than 10, pirate Then I check how many copies have been sold on steam, more than 1m, pirate

If a game dev team fails all above checks, I will still pirate first, but if i enjoy pirated copy, I'll buy the game to support the dev.