1) Create VM with config drive.

2) if 1st does not work, check "netstat -rn" (it should be able to reach/added 169.254.254.254 ?? I do not remember IP address by heart).

Because you say the Linux vms can access the the metadata service i think the installations of openstack (nova, neutron, etc) works fine. Is your windows instance has network adapter correct drivers? More simple, has your instance access to network or only console you can get? Depend of attributes in image you use the nova use different network adapter emulation. So check that your net is ok. Second think is the adapter to be configured as dhcp configuration because openstack send custom routes for ip 169.254.169.254 if you use provider networks (this is not the case in tenant networks with l3 agent). Check your route with command route print on a terminal. if your metadata service works you must get correct response for url http://169.254.169.254/.