Hi John,
I've had a read through the posts and a look at the concepts.
I think the first, as a concept, is quite appealing and could definitely go somewhere. I really wouldn't be too concerned here as the impression I get is that your guy does have an eye for design, perhaps he's just a little inexperienced in terms of his process.
Personally, I would disagree with what some people are saying here about £300 being 'a joke' (which isn't a dig, Levi). Check out Paul Rand who designed the NEXT logo for Steve Jobs back in 1986 - for a mere $100,000. He only offered one concept. It's entirely subjective.
It would of been useful to see the brief that you provided him with. A good brief really is essential. The main thing is keeping your target audience in the crosshairs. It's not about what you want, or what he wants - it's what your audience want. Who exactly are you trying to attract? Middle aged men with a high income? Or young adults who have just graduated?
To say that any of these ideas are bad, or unworthy, without proper context, really just demonstrates a lack of finesse – in my humble opinion.
He seems to understand the art of simplicity, just keep communication light and maybe halt the process if you need to reach a higher degree of clarity. Basic is not necessarily bad - and a logo alone will not facilitate success.
Feel free to reach out if you need another perspective.
Joe