The only thing I see going on with the hooves in these photos is that they are in need of a trim. The toes are shorter than the rest of the hoof wall because the horse is able to wear them down as he breaks over. So they are getting a self-trim by wearing themselves down. That would not concern me at all- my own horses do it too and are barefoot and sound. Even if the front edge wears into the sole, it has never caused a problem for me, and is really the way I think a horses foot is designed to wear! (It follows the along with the theory of Gene Ovnicek's Natural Balance trimming and shoeing: http://www.hopeforsoundness.com/educ...gene/gene.html
The rest of the hoof wall is in need of a trim, but I don't see anything bad going on there. She looks fine, just overdue for a trim.
I personally don't see why you can't learn to trim them yourself. I took a farrier science course, rode around with a farrier and then shod my own horses for years. I now just trim them and keep them barefoot, and only use Easyboots if needed on rocky trails in the summer.
These are good books to get you started if you want to learn. They are what I learned from when I decided to "go barefoot." Amazon.com: Horse Owners Guide to Natural Hoof... Amazon.com: Making Natural Hoof Care Work for You...
To me, the Rider's Rasp looks like a farce. You can get a real rasp and handle for less than 1/2 of what you would pay for a "rider's rasp" and you can actually get some work done in a quick fashion. I think the rider's rasp is just a marketing gimmic for horse owners who are afraid they will "hurt" their horses with a real rasp. I would spend the money on an education (the books) and then if you decided to trim, get some real farrier tools. One thing I would NOT skimp on is nippers. At good set of nippers is at minimum $80-100. Anything less than that is just junk that you will struggle to cut anything with.
So anyhow, if you want to learn to trim, I say go-for-it! The books (I believe) are well worth the money. And if you have a farrier you can learn from, take them up on it!