well it depends on what kind of riding you want to do. i had a very stiff boot as my first pair, because i had no idea boots had different flexibilities. now that my riding style has developed, i bought boots according to my needs. i like riding park a lot, and hitting small-medium/large jumps. im not interested in bombing down runs as much as doing flatland tricks and park, so i bought slightly more flexible boots. my boots are flex 5 (on a scale of 1-10 i think, with 1 being the most flexible).
i do a lot of park but also some begginer slopes (because i ride with friends that are begginers) but i also do flat land stuff like butter cups and stuff. what kind of boots do you have? it sounds like we're alike in riding styles