Itachi was aware of these problems peripherally, these were things he wasn't sure he could fix. Experience might teach Sasuke how to learn from his mistakes instead of being beaten down by them. Itachi had always had Shisui to keep him from brooding, though most of that was knowing that all problems could be taken to Shisui for resolution, no matter how small.
The question was, would being Jounin complicate the problem, or soothe it? Itachi had been more focused on whether Sasuke was physically ready for the rank and hadn't thought much about whether he was ready mentally or not.
Re: It's okay dear.
Itachi was aware of these problems peripherally, these were things he wasn't sure he could fix. Experience might teach Sasuke how to learn from his mistakes instead of being beaten down by them. Itachi had always had Shisui to keep him from brooding, though most of that was knowing that all problems could be taken to Shisui for resolution, no matter how small.
The question was, would being Jounin complicate the problem, or soothe it? Itachi had been more focused on whether Sasuke was physically ready for the rank and hadn't thought much about whether he was ready mentally or not.