I told this same story in another thread about how I first came to JRiver, but will repeat it here as it relates directly to Jim's question.
A friend strenuously recommended I try MC. I thought great, I have been auditioning a number of music players, why not check this one out as well. This was around 2006/2007. The friend had emailed me a link, I clicked on it and went to the site. My immediate reaction was... "Wow… This site looks really dated. Is this site legitimate? Maybe my friend's link was really old and I'm actually at their discontinued site? Are they still in business?". This was 15 years ago, and the site has not really changed in any significant way since.
This obviously is not the initial reaction you want from anyone being exposed to JRiver for the very first time. And if I had the reaction (and I am personally aware of half a dozen others who had the same reaction), how many potential new users over the last 20 years also had that reaction? Thousands upon thousands I have no doubt. In spite of my reservations, I went ahead and downloaded the trial (well it was actually the free Media Jukebox at the time), and indeed, it offered features that I really liked. My question is though, how many people had the same reaction I did, and went away without ever trying it. Or... how many of those went away, came back 2, 5, 10 years later, and saw the website had not been updated/improved, and thought "yeah, not ever gonna buy that program".
The 1st impression is everything. Site visitors turned off enough will ultimately go with a different media player. If you blow that first crack at a new customer, the chances of turning them into an MC user at some point in the future are extremely low. I can already hear some current MC users objecting saying "hey, I used to use program such and such and hated it, and I switched to JRiver". I can only say that users who switch represent the tiniest of minorities. It is simply human nature - once you have invested time in, and are comfortable with, a given program (media player or otherwise), you're not likely to switch, even if you have problems with it.
I'm not a webmaster, so I won't pretend I know specifically what it is you should do to improve your site. You should hire somebody who does that for a living. They will ask you the right questions, and then create a site that is beautiful, modern, and of course, functional.
And please remember - the super hard-core users who frequent the forum on a daily/weekly basis are NOT your entire user base. In fact, they are but a tiny slice. According to your forum stats, there are 57,000+ users. I would guess 1,000 of those are heavy forum users. And how many people who own your program never even bother to register to use the forum? I'm speculating, but I gotta think that's another 10 or 20,000 - maybe even substantially higher. Either way, there is a significant chunk of media player users, including the vast majority who use MC, who simply use it for basic music organization/tagging, to play music and look good while doing it. They're not writing expressions, not creating complex smartlist driven views, not looking for the most cutting edge DSP tools... none of that. Updating JRiver's website with those sorts of users in mind would be enormously beneficial.
I desperately hope you are not insulted and thereby completely put off by this post. You know I love this program Jim… You know I have put thousands of hours of my own time into creating skins. I desperately would love to see MC grow and grow and grow. That is my motivation - to offer some brutal honesty in the hope that it leads to changes that improve J River's bottom line, which will in-turn help MC continue to be best in class.