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This is the general conclusion I've come to: although the design itself is not very appealing, if you're the designer and have no power over the content of the book or the title, then your design shouldn't be beaten up for the fact.
That being said, I'll post what I think without the fact that I don't like the book's content and title, commenting only on how good the design within its context.
Font: The most fitting font for the title is in the first variation. To me, a sans serif font gives a more modern look to the book, which is not the objective here.
The tagline font serves its purpose.
Colours: Choice of colours is bland, but it works.
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After this point I feel the design could use some improvement.
If the $ were to look as part of the road, as Michael pointed out, it wouldn't look as out of place. The biggest problem with the bottom half of the cover is that its not "connected" to the top. There doesn't seem to be unity. Not sure how to get past this, I suppose it would require some experimentation of your part.
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Overall, I'm not a fan of the design in general, but as I said, it might work for the target audience. Do look at other covers in the same category.
Whether or not the book sells with respect to its content, the goal here is to help sell it by making a well designed cover for the target audience. Hope you find something useful in the above jumble. :)
