Jail RP was fun specifically because it was not balanced. If you want to escape you (ideally) have to be a loving genius, so when it works out you feel accomplished. In order to do so you had to explore the map, find resources, find weak points, find exploits, do whatever you could to even the odds. When you got gunned down and killed, it felt bitter, but you most likely ended up learning from the experience, so you're that much closer to escaping next round. Crowns server used to be really good for this, the map was open and nonrestrictive, you could develop creative ways to get over the walls and on the roof and in places that made it hard for the guards to keep track of you.
nu-Crown's jailbreak is a loving travesty. It took away the single benefit of being a prisoner: The guards can't just murder you for absolutely no reason. It's soulless, boring, childish, tacky. It loving sucks. You can tell yourself "different strokes for different folks" if you want, but it doesn't change the fact that the new gameplay design is objectively worse than it's predecessor by a massive margin. You can say "it's fun when you epic rebel against the evil warden!" but there's absolutely no reward or incentive to rebel, 9 out of 10 times you'll just end up dead. That's several minutes of your life vaporized because you didn't type /sit on your bed fast enough. You didn't learn anything, you were just a tool for some handicap's power fantasy. Why anyone would base their server off a game that still sucked when they were 5 years old is beyond me.
The Simon says stuff isn't necessarily the problem either. Jail RPs that don't have it still all have the same stuffty pitfalls. All the maps are built for a specific linear gameplay design in mind - Prisoners amass weapons through whatever means necessary, then go on a rampage to kill as many guards as possible. It almost always results in a stuffty TDM, but the ROE for one team is all forgeted up and if you get it wrong you can get banned from the entire server for free-killing. Map design is really key here.