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Tim, Tim is....Tim...... Yes I know Tim in the series is proven to have a mental disorder. Tim or Masky is seen in many entries Masky seen attacking Jay and Alex but Tim is seen as out secondary protagonist at one point. Masky is seen holding Alex back, is Alex dead from Masky, did Masky get revenge from Alex breaking his leg? I sure as hell don't know.
Tim and Jay seem to have had an alright relationship in the beginning, most of his appearances in the early entrys seem to have been forgotten in the later when they meet up again for the interview, even though he had been there for various scenes. Tim and Jay work together, but both seem to be suspicious of the other.
Tim is a level-headed, cautious person, but he is not afraid enough of his advisories for them to disable him.1 He has a good sense of humor, which he uses often to make light of certain situations; he seems to be a calm individual on the exterior, hiding the fact that is a scared man who only wants to escape from the hell he is in.
It could be that the pills Tim can be seen taking pills in Entry 16 which Jay finds in The House in Entry 16 and examines in Entry 19.5. These could be Painkillers, or some other form of drug, to try and help take his mind off things, perhaps because he was being stalked by the Operator. But I think it is much more likely that he was simply taking Pain Killers to help him from the pain that the Operator's pressense causes. I don't know whether I personally believe this or not, but it's certainly a possibility.
Entry 60.5 confirms that Tim has been experiencing slendersickness since at least the mid 90s and was treated at the facility that is now the burned out building that he is so apprehensive about returning to. This was many years before Marble Hornets began filming. Tim is one of if not the first person involved with Marble Hornets to encounter the Operator.
Tim is seen taking pills a number of times in the series, from season 1 when they are found in the abandoned house onwards. In the medical forms found in Entry 60.5, there is a part where anticonvulsants are referred to as a preventative measure. The pills Tim is seen taking throughout the series could easily be these same anticonvulsant medications.
One of the functions of an anticonvulsant is to "suppress the rapid and excessive firing of neurons that start a seizure" (taken from wikipedia). Neurons firing are electrical activity. The Operator has some sort of undefined effect on electrical systems, and this could easily include peoples' brains. This could mean that, while Tim is taking anticonvulsants, he is not effected by the Operator in the same way as other people are. This could include a decrease in things like memory loss and disorientation.
There is evidence from the first season that Tim was taking the pills for seizures then — Jay steals his pills, and the next time they meet Tim has an apparent seizure, and the pills get stolen back — and this is the first time specifically that we see him taking pills in the current day. In this case the pills would in fact enable Tim to be Masky but not require it, and would mean that Tim's ability to be Masky is an act of his own agency.
Tim, when on his medication, could be keeping his memory far more than your average slender-stalkee, which could itself account for the 'Masky' behavior. Rather than an alternate personality, the mask is a way from keeping the Operator from specifically recognizing Tim when Tim decides to do stuff that he's learned (over many years, apparently, of being involved in these shenanigans) agitate the Operator — ie, being on camera, taping TO, getting involved with people who are being stalked by TO.
The continued knowledge of an eldritch horror hanging around would wear on a guy, though. Two theories: Tim could have at some point decided seizures were less dangerous than continued knowledge of TO, and stopped talking his pills in order to let his memory be wiped like everyone else's before resuming his medication, or Tim could have put away the mask and distanced himself from all things Marble Hornets intentionally while still taking his pills and retaining the memories.
tl&dr; Tim takes anticonvulsants for a preexisting condition, and the anticonvuslants themselves contribute to his ability to don the mask but don't require it.
The Masked Man and Hooded Man have possibly collaborated at some point. As show in Entry 84 is possible that he already knows who is the Hooded Man.
