I have a home-grade router (Asus WL-500gp) and with MAC address "access control" being enabled (and adding to the overall delay) I haven't ever seen full timeouts. Maybe just the first request, but as long as it shoots out several, I've never seen it failing completely unless the network is disconnected.
What I can suggest you is to adjust all/one of the retries/timeout/tryagain settings for the udhcpd: Man online - udhcpc (8)
I don't have the image or Galileo in front of me to check where they set that, but it should be either in one of the init scripts under /etc/init.d or in the network config scripts under... can't recall, IIRC /etc/sysconfig/network or something.