We'll see if Harry makes a similar leap after a year with a teacher.
This would be nice, but I don't know if he will have the time. He is supposed to show up at Lara's side on several occasions, work on his trauma, repair the castle, care for Maggie, (re)establish himself as Wizard of Chicago (whatever that means), fight the occasional monster, do Winter Knight stuff, make some money, ...
I can't imagine LtW will be available as a teacher, because he is Council. Imho it is more likely that River Shoulders become his teacher. But I don't think he would come to live in Chicago, so Harry would have to go to him. Maybe even live a for a while in the forest or the reservation. So even if he can free himself for a while from his duties, what about Maggie. He would either have to take her with him or make her live with the Carpenter's again. I don't think she would agree. Leaving her would hurt her a lot. He won't do that on purpose.