On a couple of thoughts:
I recently bought a software program after trying it out from
www.workingartist.com . It's a software management program for artists. It is mainly geared toward the painter who paints works for galleries, inventory for sale, etc, and I am just now learning to adapt it to commission work. One of the things it does emphasize is the organization and management of contacts and potential clients. You can download a free trial disk to see if it might work for you.
And I do agree with the perceived problem of clients not having confidence in their own judgement - but it's a perception we can change. I absolutely think that one of the most important jobs we have is client education. Several years ago I began developing a Comparative Pricing notebook. Once people can see a context within which to evaluate your work and prices, they are extremely capable of making decisions.
Stanka's ( HI! We've missed you!) point is very significant. Don't show portfolio work if that's not what you want to paint. Show what you
do want to paint. I have had students say:"Shouldn't I paint little barefoot girls in white dresses? Isn't that what people want?"
Well, sure, some people do. But the important question is : "Is this what
you want to paint? " If so, go for it! If not, keep painting what you want, but keep in the forefront of your mind:
Whatever you paint , paint it well. You can only do your best.