Definitely start with a low dose just to get a feel for things. Going straight for a khole (no matter how much you've read about) isn't usually the best course of action with ket--it ends up scaring or confusing most people before they have a chance to learn to appreciate it. There's really no rush either so you might as well work your way up to it.
As per your music question I've gone into holes with and without music and don't have anything bad to say about either. Music ends up taking a back seat but you really just have to try it out and see for yourself.