I agree with most of what has already been said. I used to have a massive font collection but over the years I've pared it down to about 35-40 that I use most of the time. I am not a commercial artist so I don't really worry too much about copyright issues. All of my fonts come from Dafont and I always make sure to only use the ones that are licensed for "free" use. If you ever plan to do any commercial work make sure to do your homework on who owns the font and whether or not it is licensed for commercial work.