Higher or lower?

When you have a child with special needs, how do you know if you should have higher or lower expectations?  Seriously, I would looooove to hear suggestions, been there done that type of tips from parents of kids with various types of challenges.  Our annual ARD meeting is coming up and I just don't know what to ask for.  Dillon has done great the last 2 days at school.  He's happy and likes his teacher.  Right now, his IEP has him in a typical developing classroom with pullout to the Resource room for 90 minutes a day.  There they help him one on one with his work.  It is working out well(he did that last year too).  My big dilemna is at home.  He is so tired and won't do homework without a struggle.  He gets frustrated and acts like it is killing him!  I realize a lot of this is him being manipulative and such.  But, the flip side is that the work is hard for him and I don't want to frustrate him.  School must be difficult enough for kids like Dillon and I don't want him to feel inadequate at home too.  Do you push and push to make them reach harder or do you realize that they are different and relax, let it slide??  Very confusing.