I still don't understand this concept, do you want them to start on a trail to a prison where the Ts try to break off from the group and make their way to the opposite direction? If so, there would be so much chaos because the CTs would be killing off every T that's not walking in line.
CTs would not have much flexibility with orders in this case, the only order would be "Go to the prison no detours or delays" they could change it up, but not by much it would be like "Go to the prison... crouching... no detours or delays"
And since the CTs have access to guns, escaping would be pointless unless you can dodge 3 clips of bullets like nothing.
We would possibly have to create a new server just for maps like this because I feel that maps like this could interfere with the rules we already have set up, but if you guys can make it work, go for it.
It sounds like a bland idea imo, eventually you'll start seeing maps like Prison Escape Indiana Jones. You can't really do much with this and most of the times CTs will have the upper advantage.