I do think that a lot of arguments around the idea that Sam was "lying" to Jess by not telling her about hunting/not explicitly revealing everything about his family situation/childhood (it's clear she knew SOMETHING about the state of his relationships to his family), and particularly those that take the leap into saying that this is evidence that their relationship was inherently unhealthy/abusive/doomed to failure, come from a place of delegitimizing Sam's relationships outside of his family and especially outside of Dean.
I think they also miss a key aspect with regards to Sam not telling Jess about hunting. We know that (very likely) Sam's post series family do know at least something about hunting (enough for DJ to have an anti possession tat), by contrast Jess doesn't seem to have any awareness. The difference here is that when Sam left for Stanford hunting was something he could reasonably assume to be able to leave behind. At this point in time he has absolutely no awareness of the forces that have been violating his autonomy and pursues him since he was a literal baby. S1 tells us Sam and Dean weren't even really aware of demons or possession, and Bobby tells us that such things were considered rare occurrences. Sam has no reason to believe that he, having got out, is in any particular danger of being actively pursued by the Supernatural. Having spent most of his life being part of a force who are the ones who actively hunt down "monsters", reasonable to assume that stopping doing that would significantly lower your chances of being involved in a Supernatural event.
Sam wanted to leave hunting because he sought "safety" - it follows that he did in fact feel some degree of that once he had done so.
Telling Jess about hunting therefore would not necessarily be seen by Sam at this point as a necessary thing for her own agency and protection, since he was likely expecting to live out his life with her with minimal to no direct contact with the supernatural.
The circumstances by the series finale are widely different, both in terms of Sam's knowledge and Sam's noteriety amongst supernatural beings, making some form of disclosure a pragmatic approach.
These kinds of readings of Sam and Jess' relationship also play into ideas of Sam as inherently monstrous/dangerous.
