At PointAbout, we're in the midst of working the details out on the best way to price our about-to-be-released web service, AppMakr.com.
Should we price it as a SAAS (Software As A Service) with recurring charges?
Should we price it as a one-time fee?
Should we segment the pricing based of feature sets? Customer types? Company size?
What about free trials? Or site licenses? Maybe multi-user licenses? Or bundling? Or versioning? How about an advertising-supported free or "freemium" approach?
Pricing is one of those things that seems stupidly easy the first time you think about it, then maddeningly difficult the deeper you dig into it.
If you're ever faced with having to determine proper pricing strategies, I highly recommend Neil Davidson's free PDF guide, "Don't Just Roll The Dice," which you can also buy from Amazon if you want a physical copy.
At 67 pages, it's short enough for a quick read, yet packed with detailed analysis of different pricing strategies, and the pro's and con's of each.
Although we haven't yet figured all the answers out, at least we have some ideas of how to frame the problem.