The thing you really have to watch out for here if you have lower prices published is the big guys seeing that and thinking they can get your services for that much too. You have to have your story really nailed of why the 2k-5k services are worth that much more. Usually this is in the form of service level agreements, support levels, response times, security, etc.

As an anecdote, we had "small business pricing" published on our site and organizations like The World Bank, Koch, and a few others were paying $279/month which was insane. We made a few thousand a year on those plans, and a few hundred thousand on "enterprise" clients.

We don't have small business plans anymore.