Strategy Thinker, you've made some excellent points - I think your username was well-chosen!
As to whether this is a perfect prison - well, it's a Sim prison. Which is to say, it's not really meant to be an exact replica of a real-life prison. There are significant differences, some of which you haven't seen yet. But you were definitely right to be suspicious of the clocks. The reason there were 2 clocks in Ben's room is that I wanted to be sure the clock showed in screenshots, and at that point I hadn't yet decided to play with the walls up. And later I forgot to remove the extra clock.
Then again, maybe the reason Conrad & Ben's cell has an extra clock is that it's an extra-security cell - that sounds good, let's go with it.
The new kilt thing came about just because I had just discovered the new Dragon Valley kilt and wanted to get peoples' opinions about different wardrobe options for Ben. And I knew I needed to do that before he got to the prison or wait until he got out.
As for the in-flight romance, that was just Ben being Ben! With his traits of Great Kisser, Flirty and Irresistible, plus his maximized Charisma skill, romance pretty much follows him wherever he goes. The game's attraction system helps with that too. If I wrote about every romance Ben has, there would never be anything else in this story. I don't remember, but I might have not quite finished the prison at that stage, so that could have been part of the reason Ben was allowed his little in-flight romance.
But I have to admit, I was rather hoping that people wouldn't be dwelling on how Fluffy might fit into the story until Ben actually remembered Fluffy and discovered his little friend's talents.
Thanks everyone for the comments!