Salem

Me and my girlfriend were going to start playing the game but we kind of want to work together. I know I need to get settling and stake a claim which will take some time but if she goes and uses her free teleport to the wilderness will she be able to use the homestead secret to get to me. Would she have to pay 20 silver to the guide. Im just asking before I have her set out.

You can only use the guide once so if she uses it she will have to walk to you.

would there be anyway for her to figure out where I was like a waypoint or something

If you invite her to join a party with you then she will get a pointer to you, but some areas of the map are very difficult for new players to walk to from Boston.