I voted for TTOW so I'll definitely be backing you! I had a look at the Kickstarter & I like that there's lots of screenshots, you mention the different MC personalities & the character bios look pretty.
-I think your backer rewards are good ideas (the love letters, copies of your previous games, beta access, designing an outfit, creating a character, creating a scene, etc). Another idea would be a short playable scene/scenario in between the first game & the sequel, since a lot happens in that time. It could be in the game itself, as DLC, or even a text game using Twine or Choicescript. You could also add the option to buy them as DLC when the game is released for anyone that didn't back the Kickstarter. It might be too late now to suggest something extra & I'm not sure if it would take too much time away from the main game, although it's something that'd only have to be done after the Kickstarter is finished, but I just wanted to throw it out there just in case. I think anything capitalising on the ROs in general will be popular.
-It might be a good idea to get someone who isn't familiar with either game to have a look over the Kickstarter draft. Everyone on this page has probably played TROS & is already planning to buy TTOW, which makes us a bit biased and we probably don't require as much info as someone brand new who comes across your Kickstarter.
-I think it'd be helpful to make it clearer that this is a sequel to TROS, an already published game. I know you mention it in the demo section (with a link to the itchio page), but it's a bit too easy to gloss over. You might also want to add the Steam page for TROS too.
-If you're worried about the tiers & rewards being confusing, I've seen other Kickstarters provide a breakdown grid diagram to show which rewards are available in which tiers, and I think that makes it as clear as possible. There's an example of this on this current VN Kickstarter: https://www.kickstarter.com/projects/lunarisgames/errant-kingdom
-Unless I've missed it, I think it'd be a good idea to provide links to your game dev social media accounts & a clear link to your itchio store page so people can browse your previous games.
-Make sure there aren't too many early bird backer spaces. I'm not an expert on this so I'm not sure what the right proportion should be, but most people who will back a game will pick whatever the cheapest tier is that includes the base game. So take into account how many of that tier you need to sell when deciding the number of early bird spaces.
-Other people have already mentioned that a trailer would be ideal (like the one on the TROS Steam page), and if you're releasing on Steam then you'd need to make one eventually right? If that's not possible, or in addition to this, it would be cool to include some GIFs in the campaign page, to show the gameplay (making choices, sprites changing expressions, etc).
-Mini bios of yourself & anyone else who works on the game (I think there's a separate artist?), your role in making the game, how long you've been making games, your background, any fun/silly facts about yourself, etc. may help people to see the person behind the Kickstarter.