Just tell him you respect his opinion and you'd like to send him a demo to see what he thinks about it. This works for a couple of reasons. You're not asking for anything, so you're not putting him on the defensive. Just make the connection and keep checking in with the guy every few months. The goal here is to build a relationship.
Friends help friends out.
Make a friend and you'll have somebody to help you out. Just get in the door, don't ask for anything except an opinion on the first meeting, and you'll be fine. The relationship will build over time. Besides our regular promoting to media people, we would also like to create a newsletter to fans. The best way to get names for it is from people who attend your shows.