Thanks for your input.
I have to agree, that when I imagined that one day he goes to K and the next day into 1st, it just did not seem right. I would prefer slower transition, and you gave me some great ideas. I am not worried about the academics (as he is still well ahead even of the first grade), or misbehaving. My main focus in this is the emotional part. DS likes things to be consistent, fair and predictable. Although, I think once he will see that the 1st grade is just more grown up in the whole learning approach he will appreciate it.
Oh, DS didn't want to skip due to missing his teacher. We were actually able to explain to him that sometimes in life, you have to make really hard decisions, but in the end, they are the right decisions. This was a big thing for him, as he is a perfectionist, AND really gets frustrated over challenges when he can't "conqur" them right away which can in turn teach him to choose the "easy" road when making difficult decisions.
He also tends to attach himself emotionally to adults in his life. But we told him that it does not mean he would never see his teacher again. So he came up with a plan as to how he would still see her (he says good morning to her every morning before class starts).
Maybe you can work with your DS to come up with a "plan" on how to deal with the things that he will miss most or to ask him how he feels about it all and address each feeling by coming up with ideas on how to make it "easier".