Medication is an option for only some of the diagnostic possibilities (ADHD, mainly), so it shouldn't be a principal determining factor in pursuing evaluation. For the other possibilities, early, non-pharmacological, remediation can make a pretty big difference, particularly in terms of academic engagement. As long as he is happy, not only with his experience, but with his understanding of himself as a learner, waiting it out is, of course, one of your options, but if there are ongoing concerns about a suspected learning disability, it might be worthwhile investigating. If he has some kind of LD, the presence or absence of the label will not change the existence of the LD--but it may affect his access to supports that could lessen its long-term negative impact on him.
