Technically, Naoki is Shikamaru's relative right? How did he personally felt witnessing the horrible things Shikamaru had to endure when he got in trouble in Kusagakure? Did he hold himself liable for not being able to get Shikamaru out earlier? and how about Genma when he realized he lost him from his radar? Set aside their duties as ninjas under orders, did they both regret it?
Hey there Anon! Thanks for the ASK! <3
Technically, Naoki is Shikamaru's relative right?
Yes. His mother was of the Nara.
How did he personally felt witnessing the horrible things Shikamaru had to endure when he got in trouble in Kusagakure?
Naoki would’ve compartmentalised his emotions (as Tenka); but his actions later-on (blowing his entire mission) spoke volumes for how he felt about what happened to Shikamaru, despite his attempts to prevent it.
Did he hold himself liable for not being able to get Shikamaru out earlier?
Not logically, given that he’d warned Genma earlier and tried to intervene at the time. Also, he was deep undercover as Tenka -- it was weighing up his promise to the Sandaime and Shikaku’s security against the events unfolding. Logically, Naoki would have processed this all in ANBU/ROOT mode, however, he felt a lot more than he let show -- which he unleashes when Shuken crosses the abuse line.
and how about Genma when he realized he lost him from his radar?
Ah, Genma. Safe to say there is a lot tangled up in what went down and how Genma felt about it all both at the time and in the aftermath.
The answer to this specific question about feeling accountable lies in this scene between Genma and Shikamaru in UtS when Shikamaru is trying to apologise for Naoki. I’ve cut it down to mainly their dialogue, but a lot with Genma is body language and the unsaid -- action over words and all that; but his words do ring true here. Fortunately, Shikamaru doesn’t blame Genma for what happened -- and that’s both fair and mature of him.
[...] "You still don't know the first thing about me, kid."
"I know that you still call me kid like you did back at the Proctor Trials, which probably means you still see me that way. Still see the stupid, naïve, 15 year old brat that disobeyed your orders and got himself into some serious shit which caused a lot of people a lot of grief…" [...] "I know if I hadn't given you the slip, if I hadn't left that room…none of this would've happened. But it did. And while I'm grateful for everything you did to protect me, I'm sorry for everything – and everyone – that it cost you."
[...] Genma's jaw simply went from side to side, senbon grinding. "Shit happens."
"Yeah, but it happened to you. And that's on me."
"I'm not gonna argue culpability with you. I had a job. I failed. You had an order. You disobeyed. I won't make the same mistake again. Be sure you don't either."
That being said, Like Naoki, his actions translate how he felt about it. His interaction with Asuma, leaving the Sarutobi breadcrumbs -- risking the System of Lies -- speaks to his sense of guilt/regret. Naoki’s actions also speak/scream. In the end, he abandoned all conditioning and he went for Shuken, blew his own cover, and gave up everything in his final hours to try to spare Shikamaru the trauma of the memories; acts that ultimately cost him his life.
Hope this answers your questions, Anon! Thanks for the interesting ASKs regarding those two <3