I don't know much about the conditions of the jail bossman is in but I've watched way too many videos and documentaries about jail and prison that in some places it is far worse to be in jail than in prison (the Louis Theroux Miami Mega Jail doc comes to mind immediately). I doubt he's in a place that's a complete shithole but as you said jail itself is a punishment obviously no matter what.
I've posted details on his conditions before. You can peep it here:
How accurate was I?
From an article discussing the jails expansion

Damn those Bunks NCIE! They got the ladders on the ends and the under bunk drawers.
The jails superintendent looking in on the area these officers are standing in front of. this is likely an observation area or a hallway.

Whats interesting on this jails design is the separate area with the picnic tables. This is nice as you can haev some rec time and not eat in your bunk. Some jails with these dorms will make you either eat in your bunk or go to a cafeteria. Looking at this design though.
Fuck. Imagine going MONTHS without sitting in a chair with a back? The only chance you have is if you get bottom bunk and you can lean on the ladder.
Though these are pictures of the expansion, the jail consists of multiple dorms/pods of this type. They do separate some of the inmate population based on their crime/violence factor. I bet Austin is in the more violent group this time, but I do not believe he is violent acting in jail and is not in the segregated area with separate 2-man cells.
Most jails you see on TV are based off of shitty ass Los Angeles or New York jails. The rest of the US jails arent completely abhorrent unless you're in a liberal shithole. Also most of the time you see a jail in a tv show its actually showing the holding/intake area, and not the housing. Holding and intake is a fucking nightmare anywhere I've ever seen.
Prisons are a whole other bag.
Edit to add: You can read about the types of cell blocks in the facility, and how well of a job they are doing at keeping BossmanJack from Mutt's law here
https://www.cvrj.org/pdf/prea.pdf Facility description starts on page 11