A bit too much sometimes I think. Like you I am quite intuitive and he can say one or two minor comments over a long period of time and I have been able to piece them together to work out a few things that have gone on in his life. I never forget anything he tells me so sometimes it's easier than he might imagine for me to do the math. For instance he once told me he had used a certain type of therapy to treat PTSD and other times he has mentioned other things about his life allowing me to piece together what caused the PTSD. I don't particularly want this insight into his life (like others said, it's harder when you care about your T) but I can't help myself trying to work him out.
I agree you shouldn't rush into changing Ts without trying to work it out first. In a sense a sort of friend-like attachment might prove helpful in working through it.