From an amateur's perspective.
Mj has a bit of an identity crisis. Is it a complex, niche product or a mass market program? Not sure from continued observation how easy it is to be both.
Niche product: pricing somewhat important (there's an upside barrier somewhere), but a bit like high-end audiophile products. I'll pay more for a Nakamichi because it has specific atttributes that make the listening experience more enjoyable and allow me greater freedom to configure as I want. My guess: if that's where you're going, could price at up to $50. Much more tolerance in that market for the complexity of reconciling basic functions (ripping/encoding, burning)with the sophistication of the database - various custom fields, advanced viz - and the inevitable bugs that must be worked out over time. Also more tolerance for a higher price point.
Commodity: very price sensitive. Too many low-cost programs out there that perform the basic functions tolerably well within a limited range and that have strong branding. I haven't done any market research generally, since I'm an MJ fan, but my guess is that $30 is the most you can ask from rookies who just want to do the basics, and aren't that hipped on advanced tagging, for example. (Before the protests start, I'm not suggesting that function is irrelevant, just that users new to digital music won't be very interested in it.). I speculate that many users never progress beyond their first jukebox unless its non-funcitonal - all they want to do is rip, encode, play and burn, database flexibility and other add-ons less important.
This is where things get a little murky. Only so many hours in the day. We all need the freedom to prioritize problem solving. MJ 8 is concededly an advanced product, but not bug-free, from the comments of a number of users. Critically, some of those bugs affect basic operations. Time spent addressing Mini-Me issues is time not spent on other issues. And perhaps (I need help here - this is just a guess) the advanced functions incorporated in MJ may in some way contribute to problems with the basic functions.
So, to me its not pricing alone. Pricing is driven by a more basic market strategy, and its not clear to me where JRiver wants to go on this. Don't really see how you can decide price in the abstract, and not at all sure you can continue to emphasize the upper-end niche market while trying to compete successfully in the commodity market. If you're happy where you are, I think you've got room to move up on the price. If not, stay where you are and change your focus.
On free trials: they are critical to me. Like the complete version for a limited time vs the crippled freeware version, but that's personal preference. Again, a function of your basic strategy. If you're in Nakamichi-land, newcomers need to understand everything that MJ can do. Otherwise, a Yugo-version for an unlimited period may be sufficient.
HTH
BTW: I agree with Callithumpian. Read Jaundiced Eye's posting, thought it was juvenile and wrong (not one and the same), but didn't really say anything over the top - unless criticism is verboten. Forum users are pretty good at taking on simple ignorance and wrong-headedness. Don't be so risible - it sure won't help with browsers who drop into the Forum to see what's going on..
HTH