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[SPOILER FOR ECHO]

Eh? TJ's route does something for Leo's? As far as I know, the reasons as to why you should enjoy Leo's ending are just about covered in his own route; it's relatively self-contained in that way. I'd treated it as the one with the least support from other routes in delivering its climax. I'm kind of surprised that TJ's, one of the more removed from the others that does this. Can you attach a spoiler to remind me of that plot point? 

Besides that, the reason why I placed the latter 2 (TJ, Flynn) in their places is their definitive reveal of a meta issue in the narrative-- the fallibility of the protagonist Chase. The other three barely touch this on their own; at best, Leo's and Jenna's left hints. The magnitude of this reveal is dependent on how much you've established beforehand. The double-take it leads you to do is a precious thing branching mystery VN's can induce. This is Echo's design, seeing how it sprinkles exclusive interconnected lore in each route. You'd miss this experience were you to stumble upon it early.

Funnily enough, my reason for doing the Carl route first is a bit similar to yours. As it is generally deemed the least impactful, one would want to deal with it first as to avoid a valley in your escalating playthroughs. As you've also mentioned, the fact that it had a lot of lore details made it even more appealing for that.

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[Major Echo Spoilers] 

|Don't even skim Tazogor lmao|


I think this is going to come down to a difference in what you want to prioritize. The way I listed is based on having a full understanding of the story at the expense of learning some twists early, which I think the writing is more than strong enough to withstand. Most of Flynn and Jenna's routes were written post-TJ's ending so I feel even more comfortable about that.

The thing I mention with TJ is everything post car crash. TJ can't undo his seatbelt and almost drowns. Chase eventually saves him, but he immediately asks Chase about Sydney. Chase ignores him. From that point on he can't bring himself to talk to Chase. He just stares at him like he's not even human. Sam brings it up while they're in Kudzu's trailer, talking about how water was different from that point on. How he understood the fear others felt. However, all of this is written so that you can misconstrue it as this group mourning a friend and the trauma from it rather than the direct action that Chase took. Also, you miss out on what is objectively the funniest joke in Echo.

https://twitter.com/burner_flynn/status/1400941006363631616?t=YOWaw_rV-1tIC1RWf1...

Leo's route shifts the most depending on what knowledge you have. There's everything with TJ. This even shows up before the car crash, as Chase will have throwaway lines about how cute TJ is and in general has a weird protectiveness about him. (The shift in Flynn's route only happens when TJ is directly confronted.) There's the knowledge that Chase has secretly been flirting with Leo over texts that he deletes out of guilt. There's the tulpa Leo created, who is constantly threatening Chase and likely appears in front of Duke to get Chase killed. There's everything to do with Sam, which has a very different feeling if you've read The Smoke Room. And this is more of a personal theory, but I think that the Flynn that saves Chase is the cursed one. Sam at first sees red eyes and thinks it's a creature of the mines. Only after Sam recognizes him as Flynn does the scene shift and Flynn starts existing, with no red eyes to be seen. When Chase asks him how he knew about the mines he gives a very basic non-answer. With how many timeline shenanigans that exist within Echo, I really feel like Leo's is the true ending to this specific cast. That's why I suggest reading it a second time after finishing it once. There are so many small details that come together.

The reason I say Flynn and then Jenna is because of the reveal of the wendigo at the end of Flynn's route. That way when it shows up in Jenna's, you have a lot more context for it. There's a lot of emotion behind moments like it starting at Flynn when Jenna is trying to save Heather from herself and the town, or when Chase calls it Jenna's guardian angel after it saves them from Brian. Instead of being just a freaky moment, it's incredibly cathartic. Flynn has always been one of the most caring characters so his control of the town to instead save people is a moment of triumph after an ending that is very cruel.

Chase is complicated. He's a liar and he has no problem withholding things from even himself, like the texting. However, that texting confrontation is one of the most revealing moments. Far more so than that he killed Sydney. At that moment, he feels guilt, which shocks Sam into saying something along the lines of, "this is what you feel guilty about?" As he says when he's free of Sam in Flynn's route, he's glad he killed Sydney. That means he is not the one causing everything that's happening in Echo. It's actually mostly Flynn and (to a lesser extent) Leo. It's why killing Flynn delays the madness, as his guilt is cut off. It might have ended because he realized Chase did it and decided he wanted to live more than kill, but we can't know for sure. Either way, with Flynn either killed or changed, things shift. So Chase is more of a catalyst for others. I have to wonder if Chase being affected in TJ's route is because he's confused as to why TJ is doing this, since in his mind, killing Sydney was the right thing to do.

All of this is to say that despite Chase being an unreliable narrator, his motivations for doing so aren't really tied to anything deeper than basic teenage shit. It's not sinister in nature. If you don't go along with Flynn in the club, you find out Chase hasn't slept with anyone since leaving Leo, so Leo is still the only person he's been with. Chase is extremely sheltered and an awkward as fuck person. I think he should feel guilty about what he did and why Jenna's route is a little too easy for me, but it's better for the town if it's seen as a good thing so everyone can accept Sydney's death and move on. That's why I prefer Leo's ending. People move on, but nothing is washed over. TJ finally understands the weight of what happened and Chase is with someone who can help him, but is also someone Chase can protect, fulfilling both of his needs. Leo has finally taken off the damn anchor and rejects giving Chase his new number. (Again, more meaningful knowing what Chase was doing in secret.)

I'll say that Leo's route is also the one that is most directly linked with Adastra. The dream when Chase is hit by Duke has text that is almost word for word used in Adastra when describing The Other. I agree that Leo's feels the most standalone, but I really think it benefits more than any other from being read a second time.

(This was a lot so sorry if some of my thoughts are kind of scattered!)