Sometimes I think I talk WAY too much!
That is interesting! Pooh is my favorite character!

I am sometimes more like Eyeore...

But I look more like Pooh.

And I like Pooh!
His voice is so sweet...
It really depends on the CM. If they are aware of the GKTW button at the end of the ride (like if the end is the same place you "boarded")...then they may let you keep riding. They did let Lauren keep riding several times...but mainly because of her wheelchair status...to load her and unload her did not make sense...as long as people were not waiting. If people are waiting, then we did get off and if she wanted to ride again, we just went back to the beginning and did it again.
My guess is, in most cases, I would expect to have to start over. If Jake has a hard time with the walking, etc...you could talk to a CM and see if they can make an exception or something. ??
Character lines, he should get moved to the front. Some wish families have waited because the CM did not see the GKTW button...so make sure the CM at the character line sees it.
He will be having so much fun...that he probably won't notice stuff like that. If he has to go back through. I would just present it as...you get to go in the front, again!