Jessica & Tim Interactions and Parallels
Jessica-Tim parallels feel woefully unexplored to me, so I'm here to do some heavy lifting. Notes are somewhat stream-of-consciousness for now; hopefully soon I'll be able to clean them up a little more coherently.
First off, as I've said on my Jessica Character Page, I find it very interesting the way she acts in the hotel following the loss of her memory. Although it's never clear how much memory she's lost in comparison to Jay, she behaves in very similar manner to him -- sticking around the hotel in the hopes of being able to figure out what happened, roaming the town looking for potential answers, and a seemingly steadfast refusal to seek help or potential treatment for the amount of amnesia and confusion she's experiecing.
Notably, I think it's interesting how Jessica seems to act as if this is something she has experience with -- waking up in an unfamiliar place, with no idea how she got there, and being completely unable to find her way home. She seems willing and capable of rolling with the pucnhes, so to speak, as if she's done this before, or at the very least is used to experiencing something similar. Notably, she also has two particular lines of dialogue that only serve to strengthen the possibility that Jessica might be very similar to Tim as someone who may have been having repeated encounters with the Operator since she was a child.
First off, when Jay is interrogating Jessica about her knowledge of the area surrounding the hotel in Entry #31, Jay brings up Rosswood Park, and Jessica comments, "I may have been there as a kid.". I can admit that one's a bit of a loose association, but it is at least interesting that Jessica seemingly grew up in the Rosswood area just like Tim did. An arguably stronger piece of evidence would be the line from her Entry #32 confrontation with Jay -- "I keep having these dreams where I'm a little kid, and something's watching me.". This is notable because, although Jay does complain of nightmares and disrupted sleep caused by the worst of his Operator-related symptoms, I don't believe he ever indicates having nightmares of being a little kid. Implying, then, that these are less of a supernaturally-induced phenomenon and perhaps something similiar to trauma-associated memories,
Another arguable Jessica-Tim parallel would be the abrupt loss of a close friend due to Operator related bullshit. Although it's difficult to tell exactly what Tim is lying about VS what he may genuinely not remember, if he is telling the truth during the Entry #15 interview with Jay, then Tim abruptly lost contact with both Alex and - more notably - Brian after everything that happened in college. It's possible he's lying at this particular point in time, but since he does seem to have more obviously notable memory loss by the time Season Three rolls around - it'd be arguable that even if Tim was consciously working with Brian during Season One, he no longer remembers it nor any interactions he's had with Brian since the Marble Hornets film project ended. Although Amy's disappearance is something of a sideswept moment in this series, even in the comics Jessica hasn't seemed particularly moved by the mentions of her in the original videos nor in the appearance of Amy's face in Skully's collection of those they carry, it likely would have been a very notable moment in Jessica's life. Regardless of how little she remembers from the year 2010 specifically, it's a very real probability that she and Amy had been living together for a while before that particular year -- and the absence of that year from Jessica's memory would seemingly make the absence of Amy from her life an even larger hole she's unable to fill, just like Brian would have been for Tim in 2011-2012.
That makes it all the more interesting that out of all the characters who appeared in Marble Hornets, Jessica and Tim are the only two who 'made it out'. It's difficult to say specifically how much of a presence Tim had in Jessica's life before he said goodbye to her in 2014 (the comics make this somewhat more difficult to piece together -- although Jessica seems to stop watching Entries around the #32 point, Tim was a recognizable presence in very early tapes, yet Jessica doesn't point him out to Taylor as someone she does recognize, even if she doesn't know Tim's number to seek answers from him. Depending on how willing you are to take the comics 'as Canon' to the series, then mileage may vary on your interpretation of whatever relationship Jessica and Tim may have formed), but at the very least, Tim seemed to know where she was and seemed to be a major factor in whatever treatment Jessica sought after she exited the series in early 2011, based off the way she talks to him about the medications she's on.
That 'missing time' so to speak -- between Jessica's disappearance off the tapes in January 2011 to the point Tim gets reinvolved in the 'investigation' in June 2012 -- makes it a fascinating possibility that Tim and Jessica were something approaching friends during that time, close enough at least that Tim felt obligated to give her a proper in-person goodbye in 2014, rather than leaving without a word or even with just a phonecall. Especially because during that time they would have been in very similiar positions -- both experiencing pretty severe memory loss and whatever residual Operator-related symptoms they weren't quite able to shake off so early during that time period, not to mention the perceived abrupt "disappearances" of friends they were very close to at one point -- and could have found a lot of comforting solidarity in one another.
This is getting more into headcanon territory, but I do think a key difference in the "both Tim and Jessica encountered the Operator as children" history would be that I do not believe that Jessica would have been in treatment for mental health issues as a child. Canonically, because her behavior in Season Two makes me think that Jessica is very used to not seeking help for neurological issues -- Jessica doesn't give any hint or indication that she's attempted to seek medical attention or contact a doctor -- and because she speaks about the treatments in 2014 as if they're still relatively new. On a more personal interpretations/preference side of things, Jessica not having a history in the psychiatric system would fall in line with my firm belief that the Medications don't do anything to dissuade the Operator, rather the avoidance of it. Where Tim was pushed into the psychiatric system as a child and wound up severely traumatized from it, Jessica learned to work around her issues on her own, but both are adept at the kind of repression&acceptance that lead to the Operator having a diminished ability to affect them over time.