no way the saddest moment out of all those to me would have to be harry looking at his family and realising that what he wants more then anything else in the world he can never have, dd, and sirius's death sad yes but these are moment for harrys growth , these were thing that had at least enjoyed at one moment in his life but his family will never be there and the only memory of them is of only vold and thier death at least harry can look back on dd, ans sirius with found memorys, that is somthing harry will never be able to do with his family which acts as a constant reminder of 2 things

1)harry is alone

2)he will never be able to rest untill he conquers vold who conquered his loved ones.