Well I'm almost at s4 now and tho I can definitely see these ESTP tendencies in him like being generally laid back and spontaneous, but all the other things that are too Jish are still there, his denial and blame shifting is exactly like Si. I don't see him fitting one type and that's OK he's a fictional character, quite comical and outrageous at that. Yes he wants freedom, but that's not unlike a J either. When it comes to protecting others he'll take control and go behind their back like a J would.And what about now?
I don't see him as ESTJ, he has no Si compared to Chloe's ISTJ.
His drive is to "live and let live", he wants freedom and to be his own man. That's all.
Honestly, I want to discuss his type with someone who watched at least S2.
I don't think Chloe fits one type either, certainly not ISTJ. Chloe's parenting style is very P. She's quite communicative, emotionally and otherwise and doesn't show visceral controlling and overprotective tendencies which are more common to STJ parents. She's also quite comfortable opening up her feelings if the situation calls for it, like even in her job to total strangers if it's gonna help.