First, bad spelling plus bad handwriting in a kid this age? Has he been evaluated for a learning disability such as dysgraphia? Maybe it's just my bias talking, but by middle school I'd definitely check it out if there's a pernicious lack of improvement in a core area like this.

Yeah, my first thought was something like Dyspraxia.

And a diagnosis could lead to an IEP = the school may have to provide a classroom aide so he could get more intensive help.

A teacher stretched trying to cover 25 or 30 kids may not be able to give him the intensive help that he needs.