Why do I have so much font issues?

[C(-)ris]

You must reboot to clear the caches. That is just the way it works. Really, you need to look at all the fonts you have installed and figure out what the problem is. You must have some duplicates of the same font and it has no idea which one to pick. I would pick up a copy of Font Doctor and run all your fonts through that. You can also look in Font Book and fonts with the bullet next to them are conflicting or bad.