Well this discussion went down in many different paths.
All I know is the old timers like Cryptex, Frap, Dunk, Frazar, some others that I have lost contact with (real life has kept them busy), and myself used to play Jail a lot when it was Jail. When it was new and fun it was about rebelling and the craziness that ensued from that. It wasn't easy to rebel, may have been a bit easy for 1 person to escape or hide but really you had a hard time on your own.
Anyways those people listed above are veterans but I haven't seen them play in forever, well Cryptex but even my self I haven't cause all the crap I have to download. I remember when Mostly Harmless said "We will not add in skins, models, textures, as it causes too much to download and it takes too long and people will not want to stay". Original Jail was bomb planting and people didn't complain about it. Jail was rebelling and before you say "Jail has changed, blah, blah, blah" well sure but where is it sitting now?
Jail has changed way too much as Cryptex stated earlier from what it should be. Wardens should be interested in their job, guards shouldn't be dumb and get knifed from not using areas designated for them, and prisoners should want to rebel and escape not do dumb activities that just keep them busy until their teammates can a) free them, b) kill the guards, c) plant the bomb.
As nice as additional plugins are, they take away from the atmosphere of the mod. Plugins that just track stats, rep, etc are fine as they are not a bunch of downloads. I am pretty sure a lot of old timers miss the old feelings of Jail and the good ol' days. Many of the current players don't realize that was a golden age of Jail. Too many things have detracted from Jails game play to make it no longer Jail.
In before "You do not play Jail anymore, you have no power here!", still did more to help create Jail and make it popular along with the people I met especially in the early days of the mod. I still remember what it was like in those days.
Special Thanks to those that helped the Jail server in the beginning, Mostly Harmless (may his soul rest in peace), Cryptex, Dunk182, BlackestSoul, Frap, FrazarMan, Zadori (creator of the first Jail map we used [ba_jail_ego_v5/v6]), and sorry to those that haven't been on the forums in 5+ years that remember those days whose names I have forgotten, but have not forgotten those good times

!.