Second Grader?

This past year has been stressful with Logan being in first grade. I questioned in the begining of the year if I should of held him back in Kindergarten just because he was a little behind and more or less just young. He would sit and space out and (go figure) not listen as well as he should of. I should of listened to my gut reaction. Homework that should of taken 15-20 minutes was taking at least an hour. Well we made it through and he did pass first grade. (barely) Actually the only thing he got a D in was Religion ;) blame that on us. We just shouldn't of had him in a Catholic school that we would fight over who had to go to the special services that Logan would be in. After going to a very non-traditional church, sitting through a traditional Roman Catholic service was torture. Horrible and hypocritical I know. Every other class he made great improvements in. Spelling test's he would Ace, as long as I would spend hours each week with him. Math would take twice as long as it should of and he still has no concept of Money, But can read a clock and add and subtract fine.
I know Logan is on the young end of his class. I know we will have issues for years to come. Logan is smart, I have no doubt about it but he has a auditory discrimination issue just like his Father. He hears what he wants to and focuses when he wants to, if he is not pushed he will do nothing. This drives me nuts but I can also see that Erik has learned to live with it and is what most would consider successful in his job and life. I love Logan so much that just like most Mothers would do anything in the world to protect him. So I'm stuck, do I push him and spend much of our time and family time working on catching up all year, just to have him on track and get average grades. Do I hold him back a year and hope that he isn't bored and that it builds his self esteem that he thrives? I guess the answer is simple, just hard to come to. It was so much easier when he didn't know anything. The hardest part is trying to explain to him why after a whole year of working our butts of he has to repeat the 1st grade. Being a Mom sucks sometimes.
On the other end, the first week of first grade (really the first month) Logans cried almost everyday. It was killing me, and I felt guilty for even going out with the girls and doing things. I had to walk him to his room each morning. The last week of School, Logan cried almost every day, he knew he wasn't going to be in that school next year, and probably not see most of the people again. He was crying for already missing his friends and Teacher. The other day while I was out getting stuff done with the new house I was late getting back to meet him at home after school. We had a big POD (or as he called it a trailor) sitting in the driveway empty I called him and he said he was sitting in the trailor relaxing. I found him eating a yogurt, drinking a juice box with his feet kicked up as above. (note the phone on the table) he is a true boy scout I guess always prepared.