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It is a terrible, mind numbing trophy, that is for sure. Best tactic for leveling Riku to 99 is to not rush it. Unless you are on a roll, just level a few times and then do something else. It took me about 5 days. Not in in-game time, but just from when I beat the game to when I power-leveled him.
Most of the trophies for the game aren't too bad, but the Re:COM ones blow. Lvl 99 is terrible since it generally takes forever with no real shortcuts and there is absolutely no reason to be at that level, unlike KH2FM, for instance.