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There'll be a vote after every new route starts dev work as to what the next one to work on will be with all previously completed routes removed from the vote so everyone can vote again on what's left

The $25 Early Access on itch is a one off payment to get the game and have access to all future updates and content one month behind the patreon. The patreon, has access to updates a month sooner as well as the development, art and poll posts but you only have access for while you remain subbed so is more of a long term support of the game. 

The $3 tier is essentially the same as the itch purchase as the access is a month later then the $5 one however you still support more long term and get the dev posts. If you cancelled your patreon sub after getting the game you would need to resub for the next update to get that though and so on.

Yeah that's violets route lock so nothing more with her after until work starts on her post route lock content

As I say relationship is a loose term. It's mostly being his fuck toy tbh XD

And yeah Damien is nothing like Matt, in fact the two very heavily dislike each other.

Yeah Kate is a adorable and I'm definitely in the protect her at all costs club XD

As for who you can date, for the main routes it's Kate, Violet, Damien, Matt and Nathan. Nathans takes a while to date him though, as you say you're kind of just friends atm and Nathans not one to jump into things. Matt is an asshole and I'm not sure I'd even call it dating but he is one of the main options. Damien is the other guy you can get with, you meet him if you stand up for him when he's being bullied in the hallway on your first week.

You can't work on weekends, Alka labour laws and all that XD
Not going to the spa ends violets route yes, but going doesn't effect your pay so you don't actually lose out by going. 
Money wise the convenience store has multiple ways to get extra money in events as well as a pay rise, but should give you enough each month to make rent as should all jobs.

Best way to get out early is not to work there to begin with and work at the cafe instead at the start, otherwise you need to wait for someone to give you an out or to be fired

Asking Nathan out does not lead to dating him, he rejects you and ends your friendship if you do it while dating someone else.  The full dating Nathan doesn't happen till in the 90's in day count at the ice rink, he will always reject you before for either not knowing you well enough or long enough or because you're dating someone else.

As for the day 60 comment in the guide, that's out of date from before the conflict events got changed in  recent patches, some events will now trigger on set days earlier.

Be in the yearbook club and date Damien, eventually he will visit your club. Choose to blow him in the storage cupboard.

There's a full walkthrough including guides to every scene in the gallery btw in the web coursair option in the in game laptop. Here's a link outside the game too:

https://docs.google.com/document/d/1oop9YfcGfvuYI_1vuKepCPmQho_jD6oGarY6rvw7xSQ/edit?usp=sharing

Slapping and screaming at him gets him to leave you alone like you said, this only removes Matts further main sexual content and doesn't remove content from other characters so if you really hate him that's the way to go to not have to deal with him. Screaming is the most effective as that just removes any possible further harassment from him all together. That is how you get rid of him, or do you mean you want him to keep showing up but you don't want him to show up doing anything sexual, because if so he does still show up in some random school events but that's it. If you're on about ways to actually deal with him when on his route he has the most by far. You can:

1. Slap him or scream at the start of the game
2. Refuse to meet him in the bathroom then when someone spills drink in your hair don't shower it off
3. Befriend the mafia in the karaoke walk around events and then get them to deal with him on day 36 after his pet play scene
4. Tell Nathan about him and then take him up on his offer to deal with him.
5. Go down any other main route (Nathan, Damien, Violet, Kate, Bar, Bakery) and choose them over Matt in the conflict scene which will have them deal with him in some way or another.
6. Delete the pictures off his phone and literally knee him in the balls

Slap Matt at the start and stand up to Alex when he's bullying Damien in the hallway and then you can get it when walking around town.

There is an option for you to scream and it will always lead to you being rescued by either a love interest or Mr Harley. The only way to be assaulted is to not fight back and pick the accept your fate option basically choosing to let it happen