When I first heard of Escape Mode as an addition to the game I was really excited. But I have to admit that I was kind of disappoint with the game's execution. I've played through Escape Mode three times, and each run took less than two in-game day for me to escape because I could
1: Start fights/break property
2: Use a rep point to skip my punishment
3: Buff my character(s)
4: Repeat until I can start a big enough riot to escape.
I will admit that my prison is not a state of the art design you'll find on Youtube, but it's definitely not a walk in the park. What I've found is that as long as you're out of snipers' sights then your rampage can go on as long as you want to (or until the prison riot crew shows up). These are just might initial thoughts I hoped to share with the forum - please let me know if you disagree.
