Rather, in this project, it sounds like this Andrew.Tweed (the OP) attempted to solve all those problems himself, and then went shopping (shadily, I would say) for a photoshop monkey to solve his only issue, the "make pretty" part.
One of the other things you get working with a real designer is an actual relationship. When you need some collateral designed or work on a new project done, a designer that knows you and your business is invaluable. I wouldn't say it's impossible to find with some guy over the internet you paid $3000 to make your website, but I'd say it's less likely.
This may have been effective from a narrow viewpoint, but a real design process it was not.
If a company treats the people involved in its business relationships as cheap, expendable commodities - the company is not going to shine.
Selling the same work to multiple business owners is the flipside of spec'ing out to multiple designers. Think of it as a contest to see who the best businessperson is, by seeing who can derive the most business value from the same design.
If the customization/client service end is kept to a minimum, a 10% conversion would probably be a pretty nice, relatively hassle-free business. There'd be an initial investment of time in developing a stock of templates to use, but after that, a designer could probably profit off the same work for quite some time, with a minimum of effort dropping in logos, changing colors and swapping stock photos.
And for every 'contest' won, a 99designer would make way more than they could selling a single psd template—not to mention having a much more aggressive sales strategy and zero advertising costs.
It kind of makes you wonder who's exploiting who.
We all have to compete but rather than disparage a business owner for being a good steward of their money could you instead present a valid argument for using a designer as opposed to a contest? Some good reasons why a designer, that might hypothetically cost 10x more than a contest, would be better money spent in the long run, would offer a lot of value to this conversation. I feel like the last quote in your post is valid. Why would someone want to pay a lot and possibly get nothing for it? Is that not a waste of the business owner's time and money?
I'm not trolling. As a business owner on a limited budget and with clients in the same boat, I'm genuinely interested in the answer.