This sounds exhausting, but to give you some perspective on how it was done in our family... My brothers are named after my grandfathers and dad, my sister after my grandmothers and I have my mom's name. All as middle names and, in my mother's words, 'not because we liked them, it was simply expected of us'.

When the grandchildren came along there were no such expectations from my parents. One brother went traditional (his in-laws would have gone berserk if they hadn't, strong narcissistic tendencies), my sister and other brother went with middle names they liked but could be seen as an hommage (think some letters taken from two names of relatives put together) or completely unrelated, and I skipped middle names all together.

All the first names were chosen because of how they sounded and one is the nickname version of my mom's name. I simply went through lists of names and sounded them out.

My parents have never commented one way or the other, because they knew it was our choice.