I'm writing something and I'm having trouble figuring out which of these two is correct.
My gut feeling is that the first is correct and the second isn't, but also I think there might be no rule against either.
I thought the residents of EL&U might be able to confirm.
Given the context, and what I now know about X, if I had requested it under my own initiative I would expect you to have counseled me against it.
Given the context, and what I now know about X, if I had requested it under my own initiative I would have expected you to counsel me against it.
As some have pointed out, it's hard for respondents to give a good answer because they don't know what X is, nor do they know the context.
I won't give the context fully except to say it's professional negligence - X is a particular procedure which one can buy as a service from a professional.
So the context is visiting a professional with a pre-existing problem, and being offered a non-essential extra which carried a risk of causing the same problem.
Incorporating this into my first sentence would make it read like so:
Given the context of functional problems, and what I now know about X - namely that it can itself cause the same functional problems - if I had requested it under my own initiative I would expect you to have counseled me against it.
Taking all this into account, I think it might be wise to just keep things in the present:
Given what I now know about X, if I did request it under my own initiative in the same context I would expect you to counsel me against it.
What I'm trying to convey is that I expect the professional to have an obligation to counsel me against this procedure because it carries a risk of causing a problem which I already have and for which I have sought their help.