Good post Jonathan.
I have a rather controversial point of view on this.
First, the cheaper an entrance into guitar playing can be made, the better. There shouldn't be major hurdles. More new starters also increases your potential target group by the way
My own experience, when I started to play, I did not get very good advise from the retail, it was more of a rip-off - luckily I bought a Tokai strat against the advise of the shop guy (because it was red like the one of Mark Knopfler).
What is happening at the moment is an increasing importance of web forums and web sites, clips on youtube and other sites, as well as harmony central reviews etc.
Also it is rather easy to become a semi expert in no time with all the resources that are available on the internet. So today, if someone seriously wants to start guitar, he might go to a shop with already a narrowed down selection of what he wants, and will face a fight between the retailer's recommended models and the web recommendation.
Then the frustration will often be that the models that people want to try are not available, so they will either buy something else or go home and order online.
Probably retail is gonna be replaced by Online in the long term and only the big chains will survive - which is the trend in most businesses. There are always some retailers that stay small but are smart enough to use change for their own advantage.
For example why are delaers not charging for the ability to test an instrument or amplifier? It's degrading its value, so why not charge a fee?
Actually personally I can live with the current development, it is what the community wants, as long as there are still builders and people that repair stuff, which at least here in Brussels, there are plenty (independent from dealers).
The only way to change the development would be through government intervention, e.g. taxes or restrictions, but those are always bad for the consumer.