So an update since this post I thought I'd share.
The boy started third grade and his focus was still so over the place after counseling throughout the summer. We went one grading period and his grades were not what we knew he could achieve. While not being disruptive, he would do anything except the task at hand during class, and if he did he would often leave his work incomplete.
We talked with his doctor then both his teachers and decided it was time to start him on some medication, and to put aside my own anxiety about it before he wouldn't be able to make it up grades-wise.
After the first grading period we started him on 10mg Focalin extended release on weekdays and his grades have improved impressively, towards the tops of his class even.
No noticeable side effects or changes in his everyday persona otherwise. Still the same goofy kid, I just have to get his attention less during the week, until it wears off around 6-7pm.
Overall, I'm feeling good about the decision so far.