1- I don't like 50 years. I agree with DAC- if by some miracle I finally got to all three of my destination jobs, I'm probably walk away from the game (not that I haven't before, but I've come back) for good, as that would be the end of the 'goals'.
2- I still think (and it's an old problem) the baseline prestige are one of the causes. Some worlds are 80+ years in, and the top schools 80 years ago are not all the same top schools now. (Heck, some may not even have D1 basketball anymore...). Its shocking after years of saying there needs to be something that ties the baseline into the last 30-50 seasons hasn't happened. I should be able to make Illinois State into an A+ Baseline if I go to 15 straight final fours, where in HD, the baseline won't do that. If the Southern Conference has won 10 straight national championships, it should be considered equal to the BCS conferences in HD's mind. You create artificial kings of the mountain, that no matter their past successes or current trajectory are better than 200 other schools without questions with any level of competency as a coach.
3- Firings. If we insist on having the 8(?) A+ baseline schools, those schools need to have no mercy.
BUt... those are D1 Issues. They could be blamed some, but D1 isn't the only level 'low' on players.
Taking a step back, and please don't take these as sour apples... I'm okay with my ability in this game.
This game is hard.
Plain and simple. Some people figure it out in 1 RL year, others in more or less time, but very few people can wander in here and be great out of the gate. Of course, the community is very helpful, it always has been. We still cannot forget that it takes a level of work ethic and intelligence (and I believe since I still suck, luck) to figure out how the game works, and how to be good at it. It's very hard for a game that many will fail at for months to suck in new people. I wouldn't ever want that to change, but think of how the world has changed even since I found HD. Most people had a flip phone (the iPhone didn't even come out until the next summer). Very few games had online capabilities, certainally not with the ease of setup as the PS4's and XBox's of today. Facebook was still college students only. A. Some people have had THAT LONG to figure out how to be great at this game and B. the level of competition in the gaming industry has exploded. All those factors are going to hurt the game in numbers of people, even if it's on the same level as Warcraft.
On a side note to that, fundamentally, this game hasn't really changed since I found it in 2006. I think fatigue subs, potential, FSS and the removal of positions are the big ones I can recall, along with a graphical facelift (ohhhh, player faces). There have been thousands of little tweaks under the hood, but it's still basically the same game. I believe that some people here (which includes me too) forget how simply daunting this game is to figure out how to do things, what's good or bad and how to win.
Add in little frustrating things such as losing a recruit while asleep, losses that make no sense to you, entire gameplans out the window with two quick fouls and all those other little things... the big point I'm making is it takes a special kind of person to stick with this game. I had to drop it (most recently) when I had a child, as I simply didn't have enough time to be as good as I wanted to be anymore. It costs 15 bucks a season to figure out what the heck you are doing as a coach. These things are not going to attract people in 'my' generation in droves (I guess I'm the old end...). I teach High School, and while the kids are all playing Clash of Clans, or whatever the random browser/phone game of the month is (I honestly can't keep up), for free, I don't think I could even pay for them to do this game. Don't lose sight that this game is not going to get the average person to love it.
Yes, promotion is a big problem as well. In that regard (and I don't blame him) the moment Tarek cashed out, this went from someone's complete baby and livelyhood to a small hidden department in a giant company, and the fight to make it bigger went away. This is no knock on Seble or anyone else at WIS, but the reality is the game is no longer being put front and center by its owners. Now, its probably not going to change unless the hipsters decided that text based sports sims are the new rage. Somehow the small group on the 'net that love the idea of text based sports sims should be tapped into.
Lastly, someone (can't recall who and too tired to scroll back) made the point that the speed of development appears slow to the average person. I personally can't picture a staff of more than 5-10 that are truly, 100% about WIS that are programming/planning future developments. The hockey group was promised that Hockey Dynasty was next on the menu (or at least in production) in 2010. As I said before, HD is basically in the same state (outwardly) as it has been since the potential update. Versus some of the other sims on this site, HD has been pretty well loved and worked on. Reality is we're a small customer base of a small company in a small market, and changes and updates are not going to be quick. I love Eastside Hockey Manager- it took one programmer (for Sports Interactive, so he has to have some ability) the better part of 9 years to make an upgrade in his spare time that was good enough to be a new release. This group has to manage not only development, but an online community, keep the current thing running and try to spread this across 8 games with little to no overlap in their code. Patience is a good thing.
Sorry to rant so long, but I wanted to try and provide some of my perspective on the thing.