I don't like the $ sign on top for starters. Looks like something a newbie would do to add hype. It was also not very attractive to me because the W and the IF seemed to be slanting in different directions. I know they really don't, but that's the impression it gives. If you want a professional designer to put a logo together for you on the cheap, you might want to chack out 99designs.com. I've had some logos designed there and I've been happy with what I got. Good luck.
Maybe put a dollar sign behind it. My opinion is I don't like the tilt, but I could get used to it You need some gloss or shadow, I think I'd give it a 5.5/8 I don't see them at all. Part of that is my monitor (old), and I guess the other part is like you said
If you could make it look blockier (or less slanted on the edges) and get rid of the dollar sign (I like the green though), I think it would be fine.