This actually sounds exactly how I imagine homeschooling my eldest would go. It's why we don't homeschool. We've got some great teachers at his school (a Montessori) and even they struggle with motivating him to work. Now that he's 8 it's getting a lot easier, but early on he put them through the ringer. And for what it's worth, ASD and attention disorders have all been ruled out in our case.
Some things that have worked at times:
Have him guess how long each one of his tasks will take him. Give him a timer and see if he can beat the times he guessed.
Schedule play breaks throughout the day but let him know that if he chooses to play at work times, he's choosing to work at play time.
Let him plan his day the evening before. Give him some choices of works and have him write himself a schedule choosing what he will do 1st, 2nd, 3rd, etc... Choosing can be a great time waster but somehow when it's being done the night before mine seems more motivated. Perhaps because he doesn't feel the work itself is right after he chooses?
If he's a good reader, hand him a checklist in the morning. At the top, tell him what time he should be done and what the consequence is if he's not (for example: we are going to play a game together at eleven. If you aren't done, you can continue working instead of joining us). Also tell him on the sheet you arent going to nag or remind him to work. Then leave him completely alone. My DS loves the attention of nagging (which is also a lovely distraction from work). So we had to find a way to take that out of the equation.
Honestly, I have no idea if any of these would work for Bear. But they have, at times, helped my DS. Good luck!!
