My maiden name is brady we thought about using it as a middle example
[name]Miles[/name] [name]Brady[/name] [name]Bennett[/name]
Does it sound bad because of the two b’s
I think it sounds perfectly fine. I have alliterated initials, and it doesn’t sound strange. Plus I like that its a nod to your family name 
No, I don’t think it sounds bad. Hardly anyone will ever call him by all three names. [name]Love[/name] the idea of using your maiden name in the middle!
I love it!!
The way the middle name and last name sound together doesn’t matter in the least. The fact that [name]Brady[/name] is your maiden name is far more important than flow/compatibility issues. [name]Miles[/name] [name]Brady[/name] [name]Bennett[/name] is a great name.
The sound isn’t too bad, but it instantly made me think of the Moors Murders. I don’t know if that would be a big thing at all where you are, but for me the names [name]Brady[/name] and [name]Bennett[/name] together would be a huge no-no…