- buy from town / market
- wear at sanctum

i'm guessing that celeste and frey won't be in the next one since that would mean a 9 year old would be running around, unless they sent him to private school.

That is not a bad assumption. Because of the location and time difference there will some major changes to the cast in the next game. You could say that you have met the one that will continue to be a part of the main cast. A lot of the game 1 cast will show up in supporting roles and small fun bits.

Trained with Freya, helped lara choose (musical), trained with freya again and fucked her, beat the hobo and told rain not to come back.

As far as I can see the block for you is Scruffy. If you have bought the coffee machine and the PC upgrade you should have an event with him in the lounge when Celeste is not there.
This will unlock a chain of events that should lead into a lot more content.
If you have done these things and you do not get an event with him please let me know what your S.E.X number is.

The task list should note that you can get more experience from working during the evening. If it does not you should have an event in the Rec Area in the late evening.
This should unlock a bunch of path progress.

I have the coffee machine and the computer upgrade and still no luck triggering the event with scruffy, was i supposed to ask him something to trigger it or just walk into the room with him.