It's not hard to get the headache badge just go to world 1 and slide up and down the hills with the down arrow key. (Sources: Previously number 2 all time juggler (160)).
If You're having trouble with "Tools of the Trade Badge": Round 1: use sentry. Round 2 use sentry gun and one repulsor. Round 3-9 or 10 use sentinel. And when you get to 11 on (when there are 80+ enemies, use beam surge because you will make up the money pretty much in that round. Final Round. Start off with beam surge and continue to use repulsor. Once beam surge is over, use sentinel gun and keep using repulsor until beam surge is active again. Do This and you should get it! Good luck