Since Marble Hornets is at the point where Jay himself mentioned on his blog that he's having a hard time keeping their events straight, I think that a rough timeline is in order. Also, as I went to the MH Wiki to find brief summaries of the entries so that I didn't have to watch them all again, I saw that they've got the same thing here, but fuck it. I'm doing this anyway because mine's slightly different. Here's what I have so far.
enttry #37: This is self-explanatory. The footage is almost 20 years old, and there hasn't been anything else from 1991 yet.
Entry #5: This Entry is probably the first bit of Alex's footage, as it predates any sort of Marble Hornets filming, and the locations scouting implies that there's no set yet (see Entry #2).
Entry #12: Alex and Brian seem to be working on some blocking, which implies that they've done at least most of the location scouting already. It also seems to predate the "paranoia" stage Alex goes through, since Alex doesn't seem to think twice about the Operator, assuming him to be just some guy who wandered onto the set.
Entry #2: This is often believed to be the first of Alex's footage, but Alex's lines indicating that Marble Hornets already has a set places this after Entry #5, where Jay and Alex are location scouting. I would also place it after Entry #12, considering that the "tall guy" who spooks Rocky puts Alex on edge enough to check back, and Alex doesn't seem to think twice about him in this entry. This is probably the start of the "paranoia" stage.
*Entry #7: Alex seems mostly stable in this entry, but becomes instantly paranoid when he sees the Operator in the background. This could also come after Entry #1/6, but I'm going to take a guess and say that it comes earlier.
*Entry #20: I may be wrong here, but I think that this entry actually comes immediately prior to Entry #17. Tim was wearing a dark shirt under his jacket, and in Entry #17, Jay can be seen wearing a button-down collared shirt (like the one he wears in Entry #20) beneath his jacket, in addition to his brown cap. Tim also has the same water bottle, in both videos, although this may not be a good indicator, since a similar or the same bottle also shows up in Entry #16)
*Entry #17: Jay seems to be slightly affected by the events, although Tim and Alex seem mostly fine. Alex reacts with paranoia when he sees the Slender Man, much like he did in Entry #7. The dialogue also implies that something may have happened to Brian, which would have pushed Alex further into paranoia. A comment about how Alex left the camera on also indicates that this may be around the time that he started constantly recording.
*Entry #1/Entry #6: These almost certainly happened around the same time, and Entry #6 probably came after Entry #1 (since the former was at the beginning of the tape and the latter was at the end), but apart from that, it's hard to tell. The panic seems to imply that it takes place in the "paranoia" stage.
*Entry #10: Most likely occurs around the time of Entries #1 and #6, since he seems to be hurriedly fleeing, not searching.
**Entry #3: While this mishmash of clips could be from drastically different points in time, Alex seems to be in the same mindset for all of them. Because the tape from Entry #1 didn't seem to have anything else unusual on it (at least, nothing that seemed unusual at the time), the tapes these were taken from are implied to be completely filled with this sort of thing. I'm assuming that this takes place after Entry #1 and #6, just because he seems to have started filming non-stop after that point. The clips seem to range from the paranoia stage to the insanity stage. As a result, it's impossible to place the clip.
*Entry #9: Alex seems to be highly irritable, and has probably been dealing with this for a while. He's also started filming himself nonstop at this point, and becomes angry when he finds out that the camera has been off.
*Entry #4: I'd place this firmly in the "insanity" stage. Alex has stopped acting paranoid and has started acting irrationally. What reason does Alex have to be at a playground? None. It seems like he has stopped running from the Operator and started seeking it. It probably falls somewhere within the time that the clips from Entry #3 spans.
Entry #11: This probably falls around the same time as Entry #8, though since the charcoal drawings that are identifiable in the two entries are different, it's unclear which entry comes first. I'm placing it before #8 on the assumption that he hung up these drawings first and made more later.
*Entry #8: This could really go anywhere in the "insanity" stage. His behavior is reminiscent of his behavior in later Season 2 entries, which also fits in with his behavior in Entries #3 and #4.
*Entry #14: His behavior seems similar to Entry #14, and he's clearly far enough into the insanity stage that he doesn't seem particularly phased by what is arguably the most reason to be worried so far (the Operator entering his room).
*Entry #13: This is believed to have happened during the "location scouting" phase, but I'd disagree, since Alex clearly recognizes the Operator. I'd place it later, since his calm demeanor (judging by his voice and his stabler camera hand) is more reminiscent of the "insanity" stage, one shot shows a fixation with trees (like in Entry #3), and he's started using the Operator Symbol.
Entry #22: This is almost certainly the last of Alex's footage, and the lines talking about burning the tapes most likely prove it.
Introduction: This is the first "present" entry, i.e., an entry that was uploaded shortly after it was filmed. The present entries will be much easier, as they can all be placed one after another. Note that this is only the Entry. The story told within the entry of how things went down probably occurs after Entry #22, which seems to be the last Alex tape. Either way, this is the placement.
Entry #15: The second "present" entry. Another easy placement.
Entry #16: The third "present" entry. Again, easy.
Entry #18: The fourth "present" entry.
Entry #19: This is the fifth "present" entry, though it's a little harder to place, since Jay is going through recorded footage. However, the titles and upload dates reveal enough information to prove that this was recorded after Entry #18.
Entry #19.5: Another "present" entry. Probably filmed after Entry #19.
Entry #21: present
Entry #23: present
Entry #24: present
Entry #25: present
Entry #26: The last of the first set of "present" entries. Alex's footage also occurs after Entry #25, as that was uploaded in March and this tape was shot in early April.
Entry #34: This occurred very shortly after the events of Entry #26--a little over a week. There is no indication that anything noteworthy happened during that week.
**Entry #38: It's extremely hard to place this video. The order of events when Jay and Alex meet up at Rosswood park doesn't allow for this to happen and the forest looks different from the one at Rosswood park. The only two indicators I can find are the fact that Alex isn't wearing the fisheye chest cam, and Jay's skeptical attitude towards this whole thing ("did you bring me out here to tell spooky ghost stories?). It's just a wild guess, but I think that Jay and Alex may have met up before Entry #35, and this occurred during that time.
Entry #35: This quite probably happened shortly after Entry #34. We don't know if Alex and Jay met up then or had met up earlier, but the footage of Jay and Alex all seems to occur after this entry.
Entry #36: Occurs immediately after Entry #35--within the same day.
Entry #39: Jay's attempts to contact Alex imply that this takes place fairly shortly after Entry #36.
Entry #40: Alex has contacted Jay, and Jay is waiting at Rosswood park.
Entry #41: Picks up where Entry #40 left off with Jay's dropped camera being returned.
Entry #42: Jay is running through the woods after the events in Entry #40. When he gets back, his camera has already been returned. It's possible that the early parts of this entry happened at the same time as or slightly before the events of Entry #41.
Entry #43: While it's hard to place this before or after the Rosswood Park incident for sure, the fact that Jay's footage has been mostly chronological so far indicates that this mini-arc comes afterward. In addition, in the Rosswood arc, Jay seems to have no idea what's going on with Amy, which Alex explains here.
Entry #44: Seems to follow Entry #46, particularly with Alex's comments about having found Amy. Although he's mostly likely lying, all that means is that he's changed his mind about finding her since Entry #46.
*Entry #45: While harder to place, there's no reason to believe that this entry does not fall chronilogically while most of the rest in Season 2 have.
Entry #46: A comment in Entry #43 about how Jay shouldn't know where Alex lives may have prompted Jay's stalking of Alex.
Entry #47: The conversation Jay and Alex have references Jay's break-in and Jay's conversation with Jessica indicates that it takes place after Entry #44.
**Entry #29: Apart from being shot between Entry #26 (Alex most likely got the fisheye-lensed camera after the events of April 4th) and Entry #27, and (most likely) occurring in Rosswood Park, it's impossible to tell when this clip occurs, or even who shot it. It may have happened a while after Alex showed the park to Jay, but Alex could have been in it at any time during the seven months.
Entry #27: the first of the second set of "present" entries.
Entry #28: present
Entry #30: present
Entry #31: present
Entry #32: present
Entry #33: present
*Difficult to place, probably incorrect
**Near-impossible to place, almost certainly incorrect.
ANDY'S TIMELINE AS COMPARED TO THE MH WIKI'S. Note that, while I did occasionally look at their timeline while I was compiling for comparison purposes, I drew very little from this timeline, and that mine does differ quite a bit from theirs.
enttry 37 - enttry 37
Entry 5 - Entry 5
Entry 12 - Entry 13
Entry 2 - Entry 12
Entry 7 - Entry 2
Entry 20 - Entry 4
Entry 17 - Entry 10
Entry 1 - Entry 7
Entry 6 - Entry 11
Entry 10 - Entry 1
Entry 3 - Entry 6
Entry 9 - Entry 3
Entry 4 - Entry 8
Entry 11 - Entry 17
Entry 8 - Entry 20
Entry 14 - Entry 9
Entry 13 - Entry 14
Entry 22 - Entry 22
Introduction - (Introduction) [it was unlisted, but I'm 100% positive that, were it listed, it would have gone here]
Entry 15 - Entry 15
Entry 16 - Entry 16
Entry 18 - Entry 19
Entry 19 - Entry 19.5
Entry 19.5 - Entry 18 [I'm not sure why the wiki had this after Entry 19/19.5. Must have been an error.]
Entry 21 - Entry 21
Entry 23 - Entry 23
Entry 24 - Entry 24
Entry 25 - Entry 25
Entry 26 - Entry 26
Entry 34 - Entry 34
Entry 38 - Entry 35
Entry 35 - Entry 36
Entry 36 - Entry 38
Entry 39 - Entry 39
Entry 40 - Entry 40
Entry 41 - Entry 41
Entry 42 - Entry 42
Entry 43 - Entry 43
Entry 44 - Entry 44
Entry 45 - Entry 45
Entry 46 - Entry 46
Entry 47 - Entry 47
Entry 29 - Entry 29
Entry 27 - Entry 27
Entry 28 - Entry 28
Entry 30 - Entry 30
Entry 31 - Entry 31
Entry 32 - Entry 32
Entry 33 - Entry 33