Show canned hints
The best way to clear some of the harder goals is probably to get a few more teammates to help. You can coordinate with each other to look at different regions of the board to help divide up the work.
On the other hand, it's not too useful to restart over and over again in order to try to generate a board with too few words. The game will generally try to make a board with at least 100 words. It'll also try to generate at least one longer word, so be on the lookout for them for big points!
The trophies contain letters and are arranged in a 4x4 grid. You'll want to use all of the letters to spell out a 16 letter cluephrase matching the enumeration at the bottom. Since the theme of this puzzle is Boggle, the extraction involves finding words on this grid.