I play the same way you do. Every route, in every tone. I don’t stop playing a game (that I enjoy) until I have played all of the routes, back to back. Then I read other stories, and circle back to my favs and reread the crap out of em all over again. 
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I hunt achievements a lot, which incentivizes me to explore different routes. However, I typically have at least one ‘canon’ playthrough for many games.
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It depends. Most titles I only do one round, maybe two, and then move on to something else unless the story is particularly good and got my attention. This is mostly why I tend to prefer longer, bigger games over short ones.
Many games like to use the number of words they have as a selling point but the real deal for me is how many words a path has, code-excluded, because that’s more likely what I will be experiencing. 250k words spread through 3-4 paths combined with flavor text for certain choices, and code, means the actual game, from start to finish, is much smaller than it looks.
There are exceptions. Some short games can be better than long ones if the genre is right, the interest is there and the quality is above-par. Samurai of Hyuga is part of a long series of books I have played several times and have developed a love/hate relationship with. I went from just roleplaying my character and having fun, to trying to min-max every choice to get the better endings. By the end of it, I had to follow a guide because I was this close to just ripping my hair out. No function to save whenever sucks… hard.
In fact, one of the main reasons why I tend to play (and replay demos) several times is the save function. Curious how a little feature can make such a difference in my enjoyment.
usually, im just replaying to see any romance route that i haven’t play yet, or if the personality of mc rly play in game (like in each personality you’ll get the different dialogue automatically, like what they did in twc where the npc would make a comment if you behave differently than your personality). I know it will have so many pesky variable and a a freakin headache to write and code, but that usually make me go “YES” and replay it for multiple times. 
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If the book really ‘clicks’ with me I’ll definitely do some more readthroughs and explore the content on offer.
Ultimately though if I really enjoy a particular ChoiceScript book I’ll simply open the code and read the whole thing through - you get to compare all the variations of a scene and see how the author chose to structure their code - it’s quite an interesting way to experience the narratives. Some authors have put a lot of effort into creating very complex hidden code structures that the player never has the slightest idea of - such circumstances I find to be very impressive indeed.
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I’m surprised to see that there are less achievement hunters than I expected. Personally I set out to get an achievement or two during a replay, and usually stick with the same RO(s) that I liked from the first playthrough. If you make it so that there’s an achievement for every ending or possibility or whatever, I will play most of the game!
At the end of the day there are some ROs that I’m simply not interested in (Off topic ish but Grand Academy for Villains is the CoG where all the ROs are appealing to me) so I probably won’t actually read the parts with another RO besides the one I like, though I’ll choose the path just for the achievement.
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Personally, I really could not care less about achievements. My approach is to role-play and have fun rather than check a list off. Regardless of games, be it IF or FPS or RPGs. 
Here’s the only game I played for achievements… …because it is a parody, heheh! 
Achievement Unlocked - Play on Armor Games
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That’s totally valid. Personally, I have a pretty vivid imagination so I can immerse myself in a story even if I’m only choosing that path because of achievements or because I haven’t done it before, lol. I actually don’t use a self-insert character for my first playthroughs but more of something like an oc that I’ve made specifically for CoGs. I’ll admit that sometimes I’ll skim when I’m reading a part that I’m not particularly interested in, but it’s still fun to play through all possible routes. Most authors tend to set achievements for basically all possible paths anyway, (in CoG at least) so it doesn’t feel like checking off a list at all.
Me, I approach it to play as I enjoy, which spans a fair wide of personalities. I too have quite a vivid imagination, perhaps too much sometimes, heh, but I want that freedom to play as I feel fit a character, as opposed to fitting a character to choices. 
As for self-inserting, never do that. I don’t play games to play myself, but to escape into someone else’s world and imaginings. Always a apart of me in there, naturally, as I can never escape who I am.
So true about the paths, but some paths – mean or evil, however, or some RO’s, never appeal to me. Perhaps my imagination haunts me there, as I am prone to putting myself in other people’s situation and therefore hope to not cause offence or suffering – yes, even imaginary people, ha! 
The old Goody Two-Shoe curse? 
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