(One thing I have not considered is hiring a tutor to work 1:1 with him in our home. I know this was done by a couple of people I knew in Connecticut. But one family did wind up using school and/or boarding school no less, so it was a temporary thing for elementary and middle school for that family.)
While alone with my son driving in the car I asked him out of the blue if he really wants to go to school in the fall. He said no. I asked if he was ready to actually do all the work it takes and to add in more online classes in the fall if we keep homeschooling. He said no. He said he realizes that he works well for a teacher but not for me. He said he just does not feel an internal motivation to do the work just for himself, he needs external motivation from another person. He said he feels that he doesn't feel the drive to do hard work for me or to meet my deadlines but he would do it for a real live teacher. He needs the pressure from the group, from peers, and from a live in person teacher.
He turns 14 next month. I think this is a pretty darned good and accurate self-assessment, and it's a mature mindset.
He wants to go to college. He wants to work in a field that interests him but he's not sure what that is. He thinks he wants to be self-employed, in charge of himself, in a position of leadership, able to make his own decisions and rule his own life. He puts a lot of effort into things that he really wants to do. He loves to do lists and checking off things finished. He likes to feel he has met the expectations and that he has succeeded. He likes to know where he stands compared to others, that he's competent.
He also wants friends and to be part of a group. This is the main reason why looking into a 1:1 private tutor at home is not really an option. It does not fulfill all that he needs.
We are actively looking for a private school for him to attend starting in the fall for grade 9.
I have evolved to a place where thinking about him stopping homeschooling no longer makes me cry or sick to my stomach. I no longer feel the need to run to phone a friend to pour my heart out to and ask for solutions to help save homeschooling. When I think of a good fit school I think he can be inspired, can learn, can succeed, can learn study skills and things he will use also in college, find friends, and feel competent. I no longer feel terribly that our homeschool is not providing all those things.