Glad that you like it! Thank you for suggestions. I'll take notes of requested QoL updates, and most likely you'll see it in the next version.
Marks are looks good for me now. Probably not going to change it at least yet.
Flogs and Whips not going to be added to generic spanking. Spanker is too close to use whip. Floggers are just not so exciting and I have no place for it in choices box due to engine limitation.
Cane will be the last device. But in unique scenes there can be whipping.
The last clothes edict will allow to undress convicts completely, yes. But there will be no way to spank something other then butt.
There will be prison with somewhat similar mechanics as you suggested. Stay tuned :)
All employees are already planned so sorry but no helper. No rooms left :) Anyway, there will be one more section of laws and that is it.