Hi Captain Cadet,
Sad indeed to see ShipSim sliding and I'm not really sure why though I do have my own theories.
I bought SS2008 when it first came out but did not bother with it a lot as I was much more involved with the Silent Hunter series and especially SH3. There is a fantastic thriving community there which when I recently checked has also made great strides with SH5 which was condemned from all sides when it first came out. Apparently with many mods from the community it is now a worthwhile sim.
The big drawback for me is that a while ago I suffered a stroke and my short term memory is completely shot. When I eventually got back to using the computer again I found that SH3 was simply beyond my capabilities. The controls are more complicated than ShipSim and I just could not use the submarine sim.
So, I got SS2008 back out and reinstalled it and have slowly been making my way getting back to using it again. Again, it is remembering different keys which is the problem and that's why I've splurged out on the ShipDriver, hoping it will be more intuitional and make life easier.
My theory as to the relative difference in popularity in such sims is simply down to human nature. I think a lot of people get easily bored these days especially if they are just cruising the Seven Seas from A to B to C etc., whereas in Silent Hunter there is the hunter/hunted element. I must admit that there were some thrilling times when a destroyer's sonar hit you, and then even greater thrills as your whole world shook from depth charges!
Well, for me the war is over! I am now in the Merchant Marine and quite happy.
