I know he announced his retirement in his 1992 concession speech. But given that 1992 was a peculiar election and that Clinton's first two years were a disaster, do you think he privately considered it around late 1994-early 1995?
I think he would have definitely been the most electable Republican of the 1996 field, and it certainly looked like Clinton was heading for defeat at the time. Bush was also devastated by the 1992 loss, and I imagine beating Clinton would have been a great personal vindication for him.
I definitely agree with the second paragraph
For the first one, no I don't think he considered running because his sons had already launched their political careers and I think he wanted to leave the door open for one of them to run in 2000 or later.